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  • Articles: DFG German National Licenses  (17,936)
  • 1980-1984  (4,607)
  • 1975-1979  (4,794)
  • 1890-1899  (8,112)
  • 1860-1869  (423)
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  • Immunohistochemistry
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  • Articles: DFG German National Licenses  (17,936)
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Year
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  • 1
    Electronic Resource
    Electronic Resource
    Immunohistochemical reactivity of a monoclonal antibody prepared against human breast carcinoma (1984)
    Springer
    Virchows Archiv 402 (1984), S. 389-404 
    Details
    ISSN: 1432-2307
    Keywords: Monoclonal antibody ; Immunohistochemistry ; Human breast carcinoma ; Epithelial cell marker
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The reactivity profile of an IgM monoclonal antibody, MBR1, raised against the human breast cancer cell line MCF7, was studied in a variety of human tumours and non-neoplastic tissues by light microscopic immunohistochemistry. The range of reactivity included specific types of non-neoplastic epithelial cells and a number of epithelial tumours. Most mammary carcinomas reacted with MBR1, but adenocarcinomas and squamous carcinomas from different sites were also strongly positive. Different patterns of immunoreactivity were apparent in microscopically normal tissues, in tissues with inflammatory changes and in carcinomas. Heterogeneous staining, despite morphological similarities, was documented in neoplastic and non-neoplastic epithelial cells. The reactivity of MBR1 was different from that reported for other monoclonal antibodies, but revealed similarities to that of monoclonal antibodies and polyclonal sera against human milk fat globule membrane.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00734636
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  • 2
    Electronic Resource
    Electronic Resource
    S-100 protein distribution in liposarcoma An immunoperoxidase study with special reference to the distinction of liposarcoma from myxoid malignant fibrous histiocytoma (1984)
    Springer
    Virchows Archiv 405 (1984), S. 1-10 
    Details
    ISSN: 1432-2307
    Keywords: Liposarcoma ; Malignant fibrous histiocytoma ; Soft tissue neoplasms ; S-100 protein ; Immunohistochemistry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The presence and distribution of S-100 protein were studied in 63 cases of liposarcoma and 20 cases of myxoid malignant fibrous histiocytoma (MFH), using the immunoperoxidase technique. Normal adipose tissue and benign lipomatous tumours were also studied by the same technique, for purposes of comparison. In all liposarcomas, most of the adipocytes and vacuolated lipoblasts were positive for S-100 protein, although the tumour cells in non-lipogenic areas of dedifferentiated liposarcoma and the non-vacuolated giant cells with a deeply eosinophilic cytoplasm in the pleomorphic liposarcomas were devoid of S-100 protein immunoreaction products. One third of the myxoid type liposarcomas contained numerous immunoreactive, immature-appearing spindle or oval cells, reminiscent of the primitive fat organs of white adipose tissue. Conversely, none of the myxoid MFHs contained S-100 protein in the tumour cells, including the irregularly vacuolated ones. These results suggests that the immunohistochemical demonstration of S-100 protein is a useful diagnostic tool, particularly for the assessment of vacuolated tumour cells and for the diagnosis of myxoid tumours.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00694921
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  • 3
    Electronic Resource
    Electronic Resource
    Immunohistochemical study on the liver in autopsy cases with disseminated intravascular coagulation (DIC) with reference to clinicopathological analysis (1984)
    Springer
    Virchows Archiv 404 (1984), S. 229-241 
    Details
    ISSN: 1432-2307
    Keywords: Disseminated intravascular coagulation ; Liver lesions ; Thrombosis ; Immunohistochemistry ; Fibrin
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Immunohistochemical and clinicopathological studies were performed in 27 autopsy cases with indisputable DIC, which had been selected from 1,800 autopsy cases of elderly people based on the following two criteria; 1. presence of fibrin thrombi in glomeruli, and 2. presence of fresh patchy necrotic foci in myocardium and/or fibrin thrombi in splenic sinuses. A high incidence of liver lesions (22/27) was revealed in autopsy cases with indisputable DIC. The liver lesions could be classified into four groups. Group-I (Central degeneration) was characterized by massive precipitation of fibrin irregularly around the central vein, causing parenchymal damage. Group-II (Central necrosis), showed coagulation necrosis in the cental zone due to circulatory disturbance caused by either shock as a cause of DIC or abrupt cessation of blood flow into the lobules following fibrin thrombus formation in vessels of Glisson's sheath. Both group-I and -II showed a short clinical duration of DIC. Group-III (Sinusoidal thrombosis), showed the presence of fibrin thrombi in sinusoids with mild parenchymal damage and long clinical duration of DIC. Group-IV (No thrombosis), showed neither parenchymal damage nor fibrin thrombi in sinusoids, but a long clinical duration of DIC.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00694889
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  • 4
    Electronic Resource
    Electronic Resource
    Immunohistochemical demonstration of cytokeratins in endocrine cells of the human pituitary gland and in pituitary, adenomas (1984)
    Springer
    Virchows Archiv 404 (1984), S. 359-368 
    Details
    ISSN: 1432-2307
    Keywords: Immunohistochemistry ; Pituitary gland ; Pituitary adenomas ; Cytokeratins ; Intermediate filaments
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Ten non-neoplastic pituitary glands and 22 pituitary adenomas producing different hormones were studied by immunofluorescence microscopy as well as peroxidase-antiperoxidase and biotin-avidin techniques on frozen sections and formalin-fixed, paraffin-embedded material using antibodies to cytokeratin, vimentin, GFAP, neurofilament protein and different pituitary hormones. The endocrine cells in non-neoplastic pituitary glands as well as in most pituitary adenomas were cytokeratin-positive. The cytoplasmic cytokeratin distribution patterns of non-neoplastic and tumor cells were similar and typical of the type of hormone produced: GH-producing normal cells showed a paranuclear condensation of cytokeratin-reactive intermediate filaments; this accumulation was even further accentuated in GH-producing adenomas resulting in fibrous bodies (Kovacs and Horvath 1978) decorated by cytokeratin antibodies. Prolactin-producing cells showed a less intense cytoplasmic cytokeratin-specific staining with focal paranuclear accentuation in non-neoplastic as well as in neoplastic glands. ACTH-producing cells in normal pituitary glands as well as in adenomas exhibited a strong and more uniform cytoplasmic cytokeratin staining. The cytokeratin reactivity in glycoprotein hormone-producing cells of non-neoplastic tissue and adenomas was weak. Vimentin and GFAP reactivity was confined to agranular folliculo-stellate cells. The specific and different distribution patterns of cytokeratins in pituitary cells can, therefore, provide an (indirect) indication to the production of a specific hormone if immunocytochemistry fails to demonstrate hormone production.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00695220
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  • 5
    Electronic Resource
    Electronic Resource
    Elephantiasis neuromatosa (1984)
    Springer
    Virchows Archiv 404 (1984), S. 427-434 
    Details
    ISSN: 1432-2307
    Keywords: Elephantiasis neuromatosa ; Neurofibromatosis ; Electron microscopy ; Immunohistochemistry ; S-100 protein
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary An example of elephantiasis neuromatosa, an unusual variant of neurofibromatosis, coexistent with lipomatosis is presented. This dual cell population produced a diffuse swelling of the gluteal sulcus of a young female. The neurogenous origin of the spindle cell component was substantiated by immunoreactivity for S-100 protein as well as by the fine structural observation of a regular basement membrane coating and a profusion of Luse bodies. As far as can be ascertained, this is the first reported immunohistochemical and ultrastructural study of this particular variant of peripheral nerve sheath lesion.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00695226
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  • 6
    Electronic Resource
    Electronic Resource
    Immunohistochemistry of carcinoembryonic antigen, secretory component and lysozyme in benign and malignant common bile duct tissues (1984)
    Springer
    Virchows Archiv 403 (1984), S. 271-280 
    Details
    ISSN: 1432-2307
    Keywords: Carcinoembryonic antigen ; Secretory component ; Lysozyme ; Immunohistochemistry ; Common bile duct
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary An immunoperoxidase technique has been utilized for the localization of carcinoembryonic antigen (CEA), Secretory component (SC) and lysozyme (LZ) in normal and cancerous common bile duct tissues. Little or no CEA was found in the non-cancerous common bile duct tissues. SC was found in the surface epithelium and accessory gland epithelium and LZ was demonstrated only in the accessory glands. Some inflammatory cells were also positively stained for LZ. In adenocarcinoma, CEA was always present on the luminar border of the carcinoma cells, occasionally with intercellular and intracellular localization. LZ was absent, or only faintly detected in carcinoma. SC was generally distributed in well-differentiated adenocarcinoma cells, but showed a reduced intensity of staining with progressive dedifferentiation. These findings suggest that CEA, SC and LZ could be useful markers providing valuable information in the pathological diagnosis of bile duct carcinoma.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00694903
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  • 7
    Electronic Resource
    Electronic Resource
    Granular cell tumour of the mammary gland simulating malignancy (1984)
    Springer
    Virchows Archiv 403 (1984), S. 391-400 
    Details
    ISSN: 1432-2307
    Keywords: Immunohistochemistry ; Electron microscopy ; Light microscopy ; Granular cell tumour ; Mammary gland neoplasm
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Primary granular cell tumours of the breast in 35 2and 55 year old women were studied by light microscopy, transmission electron microscopy and immunohistochemistry. Light and electron microscopy revealed a neural origin of the tumours and this was further substantiated by immunohistochemical studies, with positive S-100 protein reaction and negative reactions for surface heavy and light chains, CEA, alfa-1-antitrypsin, muramidase and GFA-protein. Granular cell tumour of the mammary gland is a very rare tumour. Clinically it sometimes simulates carcinoma because of its fibrous consistency, fixation to pectoral fascia and skin retraction. The diagnosis of granular cell tumour should be included in the differential diagnosis of carcinoma of the breast. The granular cell tumour is derived from neuro-ectodermal tissue. Whether it represents a neurogenic cell-confined metabolic disturbance with lysosomal activation, or a true neoplasm remains to be elucidated.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00737288
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  • 8
    Electronic Resource
    Electronic Resource
    A method for T-antigen demonstration by a polyclonal antibody and peanut lectin; elimination of cross-reaction with naturally occurring antibodies (1984)
    Springer
    Virchows Archiv 404 (1984), S. 159-166 
    Details
    ISSN: 1432-2307
    Keywords: T-antigen ; Peanut lectin ; Immunohistochemistry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Antisera and a lectin were used to demonstrate T-antigens in colorectal carcinomas. Rabbits were immunized with red blood cells on which the T-antigen had been exposed. The obtained polyclonal antiserum and a crude lectin (PNA) prepared from peanuts were used in an immunoperoxidase technique. The crude lectin and a chromatographic pure lectin showed the same staining specificity. Different fixatives, length of fixation and buffer compositions were tested on paraplast and frozen sections. Four per cent formaldehyde preserved the antigens well in paraplast embedded tissues when fixation was shorter than 48 h. In the immunoperoxidase technique the chromatogen used was 3-amino-9-ethyl-carbazole whose staining intensity was sensitive to the H2O2 concentration. Agglutination of T-exposed red blood cells was used to assess the anti-T titre of various sera. Normal animal serum contained anti-T antibodies, and the possibility of false positive reactions and methods to avoid it in immunohistochemistry is discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00704060
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  • 9
    Electronic Resource
    Electronic Resource
    Sexual differences in the topographical distribution of serotonergic fibers in the anterior column of rat lumbar spinal cord (1984)
    Springer
    Anatomy and embryology 170 (1984), S. 117-121 
    Details
    ISSN: 1432-0568
    Keywords: Sexual dimorphism ; Serotonin fibers ; Lumbar cord ; Cremaster ; Immunohistochemistry ; Rat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Sexual dimorphism in the topographical organization of immunoreactive serotonergic fibers has been shown for the first time in the anterior column of the rat lumbar cord. A characteristic preferential arrangement of serotonergic fibers on the small cell column composed of anterior horn motoneurons, which have been proved to send their axons to the cremaster muscle, was demonstrated at the lumbar segments (L1–L2) of male rats, using the immunoperoxidase technique with antiserum against serotonin. A similar finding was also observed in female rats, but was less prominent than in males. Comparative analysis of the cell numbers and the size of neuronal somata of the aforementioned nucleus, done using retrograde transport of fluorescent dye (DAPI) via axonal fibers coursing down the genitofemoral nerve to the cremaster muscle, gave significantly larger values in males. The sexual difference in the serotonergic innervation pattern was, in consequence, surmised to be caused by the cytoarchitectonic contrast ascertained in the lumbar anterior column. Furthermore, there may be a striated muscle endowed with some active functions homologous to those of the male cremaster muscle in the female rat.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00318995
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  • 10
    Electronic Resource
    Electronic Resource
    Immunohistochemical localization of neurofilament protein in neuronal degenerations (1984)
    Springer
    Acta neuropathologica 64 (1984), S. 30-36 
    Details
    ISSN: 1432-0533
    Keywords: Neurofilament ; Neuronal degeneration ; Neurofibrillary changes ; Immunohistochemistry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The immunohistochemical localization of human neurofilament proteins was studied in a variety of neuronal changes by the peroxidase-antiperoxidase method using antisera raised against each of the subunit proteins of human neurofilament. Torpedoes of the cerebellum, axonal spheroids of amyotrophic lateral sclerosis as well as of infantile neuroaxonal dystrophy, and neurofibrillary changes in a case of Pick's disease were consistently immunostained. Occasionally, a positive immunoreactivity was also observed in Lewy bodies, in neurofibrillary tangles of progressive supranuclear palsy, and in neuritic processes of senile plaques. Neurofibrillary tangles of Alzheimer type and Pick's bodies, however, did not react with the antisera. These data indicate that the human neurofilament doesnot share major antigenic determinants of its subunit protein with either Alzheimer's neurofibrillary tangles or Pick's bodies.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00695603
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  • 11
    Electronic Resource
    Electronic Resource
    Systemic amyloid myopathy — Light-microscopic and fine-structural study of the skeletal muscles with histochemical and immunohistochemical study of amyloid (1984)
    Springer
    Acta neuropathologica 64 (1984), S. 114-121 
    Details
    ISSN: 1432-0533
    Keywords: Amyloid myopathy ; Skeletal muscle ; Histology ; Immunohistochemistry ; Fine structure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Studies were made on skeletal muscles obtained by biopsy and autopsy from a 59-year-old man with immunocyte dyscrasia and amyloidosis; he had progressive muscular stiffness with palpable tumors and ϰ-type Bence-Jones protein, but no overt myeloma. Histologically, much amyloid was seen deposited preferentially in the skeletal muscles, especially in the endo- and perimysia, forming tumors of various sizes and occasionally associating influx of amyloid into some muscle fibers, and in the smaller-sized blood vessel walls, frequently associated with extreme narrowing or occlusion of their lumina. Most muscle fibers were replaced by much amyloid or showed extensive atrophy, having a characteristic circular space under the endomysium, which was concluded to be not due to compression atrophy but to ischemic atrophy. Ischemic neuropathy was observed and seemed to be responsible for the diffuse atrophy without spaces seen exceptionally in some parts. Amyloid was shown histochemically to contain AL as the major protein component, immunohistochemically to have a close relation with ϰ-type light chain, and fine-structurally to be formed just outside the basement membrane of the blood vessels and deposited in the endo- and perimysia through perivascular infiltration. The clinicopathologic features of nine similar autopsy cases in the literature were compared with those in the present case. The causes of damage in muscle fibers and of preferential deposition of amyloid in the skeletal muscles were discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00695574
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  • 12
    Electronic Resource
    Electronic Resource
    Reduced substance P-like immunoreactivity in hereditary sensory neuropathy of Pointer dogs (1984)
    Springer
    Acta neuropathologica 63 (1984), S. 33-40 
    Details
    ISSN: 1432-0533
    Keywords: Hereditary sensory neuropathy ; Substance P ; Immunohistochemistry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Two unrelated Pointer dogs, each from a breeding of normal parents which produced three affected pups in a litter of nine, began to bite their paws at 3 and 5 months of age. Insensitivity to painful stimuli was marked in the distal parts of the limbs and receded proximally. The affected dogs were euthanatized at 5 and 20 months because of acral mutilation and infection. Changes affecting the primary sensory neurons included: small spinal ganglia with reduced numbers of cell bodies, degeneration of unmyelinated and myelinated fibers in dorsal roots and peripheral nerves, and reduced fiber density in the dorsolateral fasciculus (dlf). Since nociceptive loss was the salient deficit in a neuropathy affecting primary sensory neurons, immunohistochemical studies focused on substance P, the undecapeptide imputed to mediate nociception at the first synapse in the spinal cord and brain. The localization and density of substance P-like (SPL) immunoreactivity was studied in three control dogs and the two Pointers by the indirect antibody peroxidase-antiperoxidase method. The spinal intumescences of the control dogs contained dense SPL-immuno-reactivity in fibers of the dlf and the superficial laminae of the dorsal horn (i.e., laminae I, II, and the dorsal part of III). Immunoreactive fascicles on the lateral aspect of the dorsal horn and in the reticular process sent contributions medially to a plexiform fiber arrangement in lamina V. Medially, SPL-immunoreactive fibers were more loosely arranged in the internal third of laminae VI and VII and in lamina X. In the Pointers, the loss of primary sensory neurons was associated with notable reduction of SPL staining in the dlf and superficial laminae of the dorsal horn. In the lumbar intumescence of the older Pointer greater preservation of SPL staining in the lateral third of laminae I and II was consistent with somatotopic termination of trunkal afferents in this region. In both Pointers there was no detectable decrease in trigeminal sensitivity and the SPL immunoreactivity in the spinal nucleus of the trigeminal nerve of the younger Pointer and the corresponding control dog appeared equivalent. In the older Pointer, however, the immunoreactivity in this nucleus was decreased relative to the control. This decrease and appearance of scattered fiber degeneration in the dorsal columns of the mature Pointer suggested that fiber degeneration progresses slowly with age to include sensory systems not affected in early postnatal life. The findings in the Pointers were compared with those made in immunohistochemical studies of SP in familial dysautonomia and the mutilated foot rat.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00688468
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  • 13
    Electronic Resource
    Electronic Resource
    Amyloid-like (Congophilic) neurofibrillary tangles do not react with neurofilament antisera in Alzheimer's cerebral cortex (1984)
    Springer
    Acta neuropathologica 64 (1984), S. 243-250 
    Details
    ISSN: 1432-0533
    Keywords: Neurofibrillary tangles ; Paired helical filaments ; Amyloid-like ; Neurofilaments ; Alzheimer's disease ; Immunohistochemistry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The immunohistological properties of Alzheimer's neurofibrillary tangles (NFT) were studied by immunofluorescence with neurofilament (NF) antisera and with antiserum raised to paired helical filaments (PHF) in NFT preparations, brain smears, and cryostat sections. NFT decorated by NF antisera were Congo red-negative. Conversely, PHF antisera stained Congo red-positive NFT but failed to decorate NF-positive NFT. It is concluded that NF do not cross react with typical NFT, i.e., NFT displaying amyloid-like birefringence, under the conditions reported in this study.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00688115
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  • 14
    Electronic Resource
    Electronic Resource
    Distribution of serotonin-immunoreactivity in the diencephalon and mesencephalon of the trout, Salmo gairdneri (1984)
    Springer
    Anatomy and embryology 169 (1984), S. 193-204 
    Details
    ISSN: 1432-0568
    Keywords: Teleosts ; Serotonin ; Immunohistochemistry ; Diencephalon
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary In this paper the serotonin-containing neurons in the diencephalon and mesencephalon of the trout have been studied by immunocytochemistry. Serotonin-immunoreactive perikarya, fibres and terminals were visualized by using well-characterized antibodies to serotonin. Six areas could be demonstrated to contain serotonin-immunoreactive cellbodies. 1. A group of cells, situated ventral to the commissura posterior; 2. A region within the confines of the nucleus recessi lateralis and a few scattered cells dorsally to this nucleus; 3. Neurons, situated ventral to the recessus lateralis hypothalami, within the nucleus tuberis inferior; 4. Cells which are situated within the borders of the nucleus recessi posterioris; 5. A number of cells, situated within the nucleus raphes superior and finally: 6. Perikarya, located dorsolateral to the nucleus raphes superior. The following three regions showed a very high density of serotonin-immunoreactive fibres and terminals: A. the most dorsal portion of the nucleus diffusus tori lateralis; B. the area dorsal to the recessus lateralis and C. the area surrounding the recessus posterior.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00303149
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  • 15
    Electronic Resource
    Electronic Resource
    Immunohistochemical demonstration of the serotonin neuron system in the central nervous system of the bullfrog, Rana catesbeiana (1984)
    Springer
    Anatomy and embryology 169 (1984), S. 219-229 
    Details
    ISSN: 1432-0568
    Keywords: Serotonin ; Immunohistochemistry ; Central nervous system ; Frog
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The distribution of serotonin immunoreactivity in the brain of the bullfrog (Rana catesbeiana) was studied, using the peroxidase-antiperoxidase (PAP) immunohistochemical method with serotonin antiserum. The somata of the serotonin neurons were mainly located in the raphe regions of the brain stem from the level of the caudal mesencephalon to that of the spinomedullary junction. A small number of serotonin neurons were also distributed as crebrospinal-fluid contacting neurons in the preoptic recess organ (PRO), the paraventricular organ (PVO), and the nucleus infundibularis dorsalis (Nid). In the raphe region, these serotonin neurons formed nearlycontinuous bilaterally-symmetrical cell columns along the caidline of the brain stem, divided into lateral and medial groups. The medial group was further subdivided into rostral and caudal parts. Processes of the serotonin neurons were widely distributed in the central nervous system, forming dense networks in various regions. The greates concentrations of these fibers were in the nucleus medialis speti, lateral portion of striatum, nucleus corporis geniculi, nucleus entopeduncularis, periventricular gray of ventral hypothalamus, optic tectum, nucleus isthmi, nucleus interpeduncularis, dorsal edge of medulla oblongata, and fasciculus solitarius.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00315627
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  • 16
    Electronic Resource
    Electronic Resource
    Immunohistochemical localization of cardiodilatin in myoendocrine cells of the cardiac atria (1984)
    Springer
    Anatomy and embryology 170 (1984), S. 123-127 
    Details
    ISSN: 1432-0568
    Keywords: Heart Atrium ; Myoendocrine cells ; Cardiodilatin ; Peptide hormone ; Immunohistochemistry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Region-specific antibodies against synthetic N-terminal fragments of cardiodilatin (CDD) were raised in rabbits and used for the immunohistochemical detection of this new peptide hormone in the myoendocrine cells within the cardiac atria of several species. The peroxidase-antiperoxidase (PAP) and fluorescein isothiocyanate (FITC) immunohistochemical methods gave identical results of cardiodilatin-immunoreactivity (CDD-IR) within the tissue. In addition to the porcine right atrial appendage, myoendocrine cells with CDD-IR were also detected in the left atrium of porcine heart, as well as in other species such as dog and cat. The exact localization of the immunoreactivity in specific secretory granules was mostly related to the Golgi-area which is located on both nuclear poles of auricular myoendocrine cells. The results confirm that cardiodilatin is stored in secretory granules observed through electron microscopical means. This hormone is most likely synthesized and released in myoendocrine cells, exerting its important cardiovascular effects.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00318996
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  • 17
    Electronic Resource
    Electronic Resource
    Serotonin nerve fibers in the primary visual cortex of the monkey (1984)
    Springer
    Anatomy and embryology 169 (1984), S. 1-8 
    Details
    ISSN: 1432-0568
    Keywords: Serotonin ; Primary visual cortex ; Monkey ; Ultrastructure ; Immunohistochemistry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary A quantitative and immunoelectronmicroscopical analysis of serotonin nerve fibers in the primary visual cortex of the monkey (Macaca fuscata) was made using a sensitive immunoperoxidase method for serotonin. The overall numerical density of serotonin-containing varicosities in the primate striate cortex was approximately 770,000/mm3 and the highest concentration of immunore-active varicosities (ca. 1,400,000/mm3) was observed in the upper portion of layer IVc, the next highest concentration being in layer IVb (ca. 1,180,000/mm3). At the ultrastructural level, the electron dense immunoreactive products were observed in the small granules (10–65 nm in diameter). The varicosities were usually small (0.5–1.0 μm in diameter) and made contact with both stellate and pyramidal cells. Serotonin fibers were often in close apposition to the poorly myelinated axons in layers IVb, V, and VI, and they rarely formed distinct synaptic structures with unlabelled neuronal elements.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00300581
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  • 18
    Electronic Resource
    Electronic Resource
    An immunohistochemical study of somatostatin and neurotensin positive neurons in the septal nuclei of the rat brain (1984)
    Springer
    Anatomy and embryology 170 (1984), S. 1-10 
    Details
    ISSN: 1432-0568
    Keywords: Somatostatin ; Neurotensin ; Immunohistochemistry ; Septum ; Basal forebrain ; Rat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Antibodies to the neuropeptides somatostatin (SOM) and neurotensin were used to study the distribution of the two peptides within the septum of the rat brain. In colchicine treated rats, numerous somatostatin-positive cell bodies were found in the dorsal and ventral subdivisions of the alteral septum, along the border of the nucleus accumbens, in the ventral tip of the horizontal limb of the diagonal band of Broca as well as in the anterior hippocampal rudiment, infralimbic area and several other structures of the basal forebrain (e.g., nucleus accumbens, olfactory tubercle and substantia innominata). Cell bodies containing immunoreactivity for neurotensin were situated in the intermediate and ventral subdivisions of the lateral septum, the medial septal nucleus, the diagonal band of Broca, the rostro-medial continuation of the substantia innominata and the olfactory tubercle. In untreated rats, somatostatin positive processes formed terminal plexuses in the medial septal nucleus and along an area close to the ventricular wall of the lateral ceptal nucleus. Other septal nuclei, such as the diagonal band of Broca contained a sparse innervation by somatostatin positive fibers. In contrast, the nucleus accumbens olfactory tubercle, and the substantia innominata contained a rich innervation by somatostatin positive axons and terminals. Within these structures the density of SOM positive processes show great variations with patches of densely packed terminals separated by areas of sparser or no innervation. The neurotensin positive terminals were situated predominantly within the intermediate part of the lateral septum and the medial septal nucleus. Both of these regions contained numerous pericellular baskets of neurotensin positive terminals around septal neurons. In addition to the septal innervation, several of the basal forebrain structures were rich in neurotensin positive processes with the densest innervation found in the nucleus accumbens and substantia innominata. Like the SOM-immunoreactivity distinct islands of dense neurotensin innervation separated by less or no innervation occur throughout the basal forebrain. Taken together, these findings suggest that somatostatin and neurotensin occur in separate neuronal populations and that each may influence important physiological functions within the individual septal nuclei.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00319452
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    Electronic Resource
    Electronic Resource
    Langerhans cells in various benign and malignant pigment-cell lesions of the skin (1984)
    Springer
    Archives of dermatological research 276 (1984), S. 283-287 
    Details
    ISSN: 1432-069X
    Keywords: Langerhans cells ; Immunohistochemistry ; Pigment-cell lesions ; Skin
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary We used immunohistochemistry to study Langerhans cells (LCs) and the composition of the dermal inflammatory infiltrate both in normal skin and in biopsies from various benign and malignant pigment-cell lesions. In normal skin and most benign pigment-cell lesions, epidermal LCs are regularly distributed. OKT6-Positive cells outnumber the OKIa-positive cells. The inconspicuous dermal infiltrate studied in these biopsies was composed of helper and suppressor/cytotoxic T cells and some dermal LCs. More epidermal LCs with an abnormal cytologic presentation were found in a halo naevus and in the radial growth part of primary malignant melanomas. This finding was associated with a dermal infiltrate composed of suppressor/cytotoxic T cells, suggesting a defense mechanism of the host towards abnormal melanocytes. Epidermal LCs were rare in the central part of the biopsies which showed a primary malignant melanoma in its vertical growth. A dermal inflammatory infiltrate was absent in that area. These findings are interpreted as the morphologic expression of a damaged immune system.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00404618
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  • 20
    Electronic Resource
    Electronic Resource
    The structure of pseudomeissnerian corpuscles (1984)
    Springer
    Acta neuropathologica 63 (1984), S. 174-176 
    Details
    ISSN: 1432-0533
    Keywords: Pseudomeissnerian corpuscles ; Neurofibroma ; Giant nevus ; Immunohistochemistry ; S-100 protein
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Immunohistochemical staining for S-100 protein was carried out on one case of von Recklinghausen's neurofibroma and one of giant congenital nevus. Uniformly positive staining was ootained in all cells of the numerous pseudomeissnerian corpuscles in both cases. These structures thus appear, like the true Wagner-Meissner tactile nerve endings, to consist entirely of Schwann cells and not to contain any demonstrable perineurial component.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00697200
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  • 21
    Electronic Resource
    Electronic Resource
    Borna disease of horses (1984)
    Springer
    Acta neuropathologica 64 (1984), S. 213-221 
    Details
    ISSN: 1432-0533
    Keywords: Encephalitis ; Borna disease virus ; Immunohistochemistry ; Axonal transport ; Cytoplasmic filaments
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The brains of eight horses that had suffered from natural Borna disease were examined with virologic, immunohistological, and electron-microscopic methods. All brains harbored infectious virus as shown by inoculation of experimental animals. Regional assessment of the infectivity exhibited the highest titers in the hippocampus and piriform cortex and the lowest in the cerebellum. Coventional histology yielded pathologic alterations very similar to those of the classical description of the disease. Immunohistology demonstrated the highest amounts of Borna disease virusspecific antigen in the nuclei of neurons. In the perikarya, dendrites, and axons smaller amounts of antigen were found. A comparison of the antigen distribution with the inflammatory reaction established a high concordance of these two parameters. The presence of virus-specific antigen seems to trigger the exsudation of inflammatory cells, which reflect the extension of the infectious process. Heavy inflammatory exsudates in the white matter underlying diseased cortical areas can be explained by the axonal presence of virus-specific antigen. Virus particles could not be demonstrated with the electron microscope. The most significant findings at the ultrastructural level were stacks of fine filaments, adhering closely to cytoplasmic cisterns. These structures might be related to virus components or might be involved in virus morphogenesis.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00688111
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  • 22
    Electronic Resource
    Electronic Resource
    GFAP, FVIII/RAg, Laminin, and fibronectin in gliosarcomas: An immunohistochemical study (1984)
    Springer
    Acta neuropathologica 63 (1984), S. 108-116 
    Details
    ISSN: 1432-0533
    Keywords: Gliosarcoma ; Immunohistochemistry ; GFAP ; Factor VIII/RAg ; Laminin ; Fibronectin
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary GFAP, Factor VIII/RAg, laminin, and fibronectin were immunohistochemically investigated in 15 glioblastomas and 15 gliosarcomas. GFAP was found variably positive in the glial areas. F VIII/RAg characterizes the endothelial cells and in gliosarcomas suggests the origin of the sarcomatous component from the endothelial proliferations. Laminin separates the two components and characterizes the inner and the outer basement membranes in the vessels. It is multiplied and thickened in endothelial proliferations, while it is often fragmented in the larger vessel wall proliferations. Our observations confirm that gliosarcoma represents the last stage of a process which starts with the endothelial hyperplasia of glioblastoma.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00697192
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  • 23
    Electronic Resource
    Electronic Resource
    Immunohistochemistry of folliculo-stellate cells in normal human adenohypophyses and in pituitary adenomas (1984)
    Springer
    Acta neuropathologica 65 (1984), S. 35-40 
    Details
    ISSN: 1432-0533
    Keywords: Immunohistochemistry ; Folliculo-stellate cells ; Pituitary gland ; Pituitary adenoma ; S-100 protein
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Presence and distribution of S-100 protein (S-100), neuron-specific enolase (NSE), cytokeratin polypeptides, glial fibrillary acidic protein (GFAP), vimentin, actin, lysozyme and pituitary hormones (prolactin, hGH, ACTH, β-FSH, β-LH, β-TSH, alpha subunit) in folliculo-stellate cells (FSC) were studied in seven normal human pituitary glands and 28 pituitary adenomas using peroxidase-antiperoxidase and the avidin-biotin immunohistochemical techniques. Approximately 5% of the cells of the adenohypophysis were agranular, non-hormon-producing FSC most of which showed a conspicuous and strong reaction with S-100 antibodies but some were, in addition, GFAP- and vimentin-positive. In contrast to endocrine cells (EC), FSC were not decorated by antibodies to NSE or cytokeratins. In addition to supportive functions, these cells, due to their close special relationship to EC, seem to have transport and other metabolic functions yet to be elucidated. By their S-100 reactivity and their distribution FSC are comparable to glial cells of the central and schwann and satellite cells of the peripheral nervous system (PNS) as well as to supportive cells in neuroendocrine organs and related tumors (e.g., pheochromocytomas, paragangliomas, carcinoids). With one exception, S-100 reactive FSC were not found in pituitary adenomas. The immunohistochemical demonstration of S-100 protein in pituitary tissue is, therefore, a reliable aid in the discrimination between adenomas and normal pituitary tissue, particularly in small and poorly preserved specimens. In one adenoma FSC were found in addition to ACTH-producing tumor cells. This seems to be an extremely rare event suggesting a combination tumor.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00689825
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  • 24
    Electronic Resource
    Electronic Resource
    Immunohistochemical localization of extravasated serum albumin in the hippocampus of human subjects with partial and generalized epilepsies and epileptiform convulsions (1984)
    Springer
    Acta neuropathologica 65 (1984), S. 25-34 
    Details
    ISSN: 1432-0533
    Keywords: Blood-brain barrier ; Immunohistochemistry ; Astrocyte ; Epilepsy ; Hippocampus
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Human serum albumin-like immunoreactivity was detected by the peroxidase-antiperoxidase method in histological sections of the hippocampus from epileptic and control brains obtained on routine autopsies. In the hippocampi of epileptic patients immunoreactive astrocytes were found, the number of which was increasing with the severity of the manifest convulsions. The highest numbers of immunoreactive astrocytes were observed in those patients who died in status epilepticus. Hippocampi from control patients with no neurologic disorders in life were devoid of immunoreactive astrocytes. The results are discussed in terms of the breakdown of the blood-brain barrier during epileptic seizures.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00689824
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  • 25
    Electronic Resource
    Electronic Resource
    Endocrine cells in extrahepatic bile duct carcinoma (1984)
    Springer
    Journal of cancer research and clinical oncology 108 (1984), S. 331-335 
    Details
    ISSN: 1432-1335
    Keywords: Extrahepatic bile duct ; Carcinoma ; Endocrine cell ; Immunohistochemistry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary A total of 44 extrahepatic bile duct carcinomas comprising 13 well-differentiated adenocarcinomas, 25 moderately differentiated adenocarcinomas, and 6 poorly differentiated adenocarcinomas were examined histologically and immunohistochemically for somatostatin, gastrin, and glicentin. Argyrophil cells, argentaffin cells, and somatostatin- and gastrin-immunoreactive cells within the tumor were detected in 46.2%, 15.4%, 23.1%, and 15.4% of well-differentiated adenocarcinomas, and in 16.0%, 8.0%, 12.0%, and 4.0% of moderately differentiated adenocarcinomas, respectively. No tumor tissues of poorly differentiated adenocarcinomas contained endocrine cells. A statistically significant difference in the frequency of argyrophil cells was observed between well and poorly differentiated adenocarcinoma. The incidence of argyrophil cells and somatostatin-immunoreactive cells in nonneoplastic mucosa adjacent to well-differentiated adenocarcinoma was higher than in that adjacent to poorly differentiated adenocarcinoma. Glicentin-immunoreactive cells could not be demonstrated either in tumor tissue or in nonneoplastic mucosa of the extrahepatic bile duct. With reference to the histogenesis of extrahepatic bile duct carcinoma, it was assumed from these results that the development of well-differentiated adenocarcinoma might be closely related to the occurrence of endocrine cells and that poorly differentiated adenocarcinoma might develop from ordinary mucosa.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00390467
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  • 26
    Electronic Resource
    Electronic Resource
    Immunofluoresceuce study of secretory epithelial markers in pleomorphic adenomas (1984)
    Springer
    Virchows Archiv 403 (1984), S. 291-300 
    Details
    ISSN: 1432-2307
    Keywords: Pleomorphic adenomas ; Immunohistochemistry ; Lactoferrin ; Carcinoembryonic antigen ; Secretory component
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Amylase (Am), lactoferrin (Lf), lysozyme (Ly), secretory component (SC), epithelial IgA, and epithelial IgM were traced by paired immunofluorescence staining in ethanol-fixed specimens from 15 pleomorphic adenomas of the parotid gland. Epithelial elements positive forsome of the markers were detected in a variable number of the specimens (Am, 0; Lf, 11, Ly, 2; CEA, 6; SC, 11; IgA, 9; and IgM, 6); their expression seemed to depend on a certain degree of glandular differentiation. Variable co-expression of secretory epithelial markers probably reflected different degrees of differentiation, indicating that clonal diversification may explain the histological complexity of pleomorphic adenomas. The most consistent expression (in almost 75% of thespecimens) shown by Lf and SC might further reflect histogenetic relationship to intercalated ducts in which these antigens are normally found in largest amounts.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00694905
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  • 27
    Electronic Resource
    Electronic Resource
    Distribution of collagen types I and III and basal lamina in human gastric carcinoma: An immunohistochemical and electron microscopic study (1984)
    Springer
    Virchows Archiv 403 (1984), S. 313-322 
    Details
    ISSN: 1432-2307
    Keywords: Gastric carcinoma ; Scirrhous carcinoma ; Collagen ; Immunohistochemistry ; Electron microscopy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Collagen types I and III were examined immunohistochemically in 32 cases of gastric carcinoma classified as poorly differentiated adenocarcinoma with scirrhous stroma, well differentiated adenocarcinoma with intermediate stroma, or poorly differentiated adenocarcinoma with medullary stroma. In the stroma of scirrhous carcinoma, types I and III collagens were distributed abundantly in fibrillar or granular patterns with little difference in the intensity of staining. In well differentiated adenocarcinoma, type I collagen was diffusely distributed in the stroma with type III collagen distributed sparsely. In poorly differentiated adenocarcinoma with medullary stroma, the two types of collagen were only found around capillaries, constituting the tumor interstitium. Electron microscopic examination of scirrhous carcinoma showed tumor cells partially covered with fibroblasts, and discontinuous basal lamina, collagen fibers and microfibrils present between tumor cells and fibroblasts. In well differentiated carcinoma, tumor cells were surrounded by fibroblasts, and well developed basal lamina was observed beneath the tumor cells. In poorly differentiated carcinoma with medullary stroma, the stroma consisted of capillaries and very few fibroblasts with discontinuous basal lamina occasionally being present between tumor cells and fibroblasts.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00737282
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  • 28
    Electronic Resource
    Electronic Resource
    Immunohistochemical study on the morphology of enterochromaffin cells in the human fundic mucosa (1984)
    Springer
    Cell & tissue research 235 (1984), S. 703-705 
    Details
    ISSN: 1432-0878
    Keywords: Enterochromaffin cells ; Serotonin ; Immunohistochemistry ; Man
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary The morphology of enterochromaffin (EC) cells in the human fundic mucosa was investigated at the lightmicroscopic level by means of the unlabeled peroxidase anti-peroxidase method, with the use of a highly specific anti-serotonin serum. EC-cells in the human fundic mucosa were sparsely distributed below the neck portion of the gland, but were found to be rather numerous in its lower half. Immunohistochemistry revealed marked pleomorphic and seemingly polynuclear EC-cells or cells with long, sometimes multipolar cytoplasmic processes. In addition, luminal contacts and contiguity between EC-cells, or interglandular connections were also encountered. The present immunohistochemical procedure permits, for the first time, a clear-cut morphological visualization of the entire population of EC-cells, and reveals the distinctive morphological features of these cells in the human fundic mucosa. These morphological findings imply that EC-cells in the fundic mucosa may be crucial in gastric function.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00226973
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  • 29
    Electronic Resource
    Electronic Resource
    Catecholamine-containing pancreatic islet cells of the domestic fowl (1984)
    Springer
    Cell & tissue research 237 (1984), S. 239-244 
    Details
    ISSN: 1432-0878
    Keywords: Islet A cell ; Catecholamine ; Combined microscopy ; Immunohistochemistry ; Fowl
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary In an attempt to identify pancreatic islet cells emitting formaldehyde-induced fluorescence (FIF), the pancreatic islets of the domestic fowl were studied by combined fluorescence, ultrastructural, silver-impregnation and immunohistochemical methods in the same section or in consecutive semi-thin and ultra-thin sections. The results indicate that islet cells emitting intense FIF exhibit a strongly argyrophil reaction with the Grimelius' silver method and also immunohistochemical reaction with anti-glucagon serum, but not with anti-5-HT serum. Therefore, the fowl islet A cell, a peptide hormone-producing cell, stores simultaneously catecholamine as biogenic amine. The islet B and D cells did not display any FIF, any argyrophil reaction with the Grimelius' silver method, or any immunoreactivity with anti-glucagon or anti-5-HT sera. The fluorescent but non-argyrophil cells dispersed in the exocrine acinus may well be PP cells.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00217141
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  • 30
    Electronic Resource
    Electronic Resource
    Serotonin and opsin immunoreactivities in the developing pineal organ of the three-spined stickleback, Gasterosteus aculeatus L. (1984)
    Springer
    Cell & tissue research 237 (1984), S. 559-564 
    Details
    ISSN: 1432-0878
    Keywords: Pineal complex (pineal and parapineal organs) ; Development, ontogenetic ; Photoreceptor cells ; Immunohistochemistry ; Serotonin (5-HT) ; Opsin ; Teleost (Gasterosteus aculeatus)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary 5-hydroxytryptamine (5-HT, serotonin)- and opsin-immunoreactive sites were studied in the developing pineal complex of the stickleback, Gasterosteus aculeatus L., by use of light-microscopic indirect immunoperoxidase techniques. 5-HT immunoreactivity first occurs in the pineal organ at the age of 80 h after fertilization and appears to be localized in cells of the photoreceptor type. The outer segments of a few pineal photosensory cells exhibit opsin immunoreactivity at the age of 84 h after fertilization. The number of cells seems to increase until the pineal organ is completely developed. The increase in the number of 5-HT immunoreactive perikarya runs parallel in time to that of the opsinimmunoreactive outer segments. The cells of the parapineal organ show neither opsin nor 5-HT immunoreactivity. The retina of the embryonic stickleback does not display opsin immunoreactivity until after hatching, which takes place about 144 h after fertilization. These results suggest, in the three-spined stickleback, an earlier light-perception capacity for the developing pineal organ than for the retina.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00228440
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  • 31
    Electronic Resource
    Electronic Resource
    Ontogeny of endocrine cells in the gut of the insect Periplaneta americana (1984)
    Springer
    Cell & tissue research 238 (1984), S. 421-423 
    Details
    ISSN: 1432-0878
    Keywords: Gut endocrine cells ; Ontogeny ; Immunohistochemistry ; Pancreatic polypeptide ; Insect
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary The ontogeny of the endocrine cells of the gut of the cockroach Periplaneta americana was studied by immunohistochemistry. During embryogenesis, the midgut begins to be formed as an outgrowth of the foregut and hindgut invaginations. Gut endocrine cells with pancreatic polypeptide (PP)-like immunoreactivity begin to appear at the anterior and posterior ends of the forming midgut. These cells are restricted to the midgut epithelium, and no mitotic cells with PP-like immunoreactivity are observed. These results strongly suggest that the gut endocrine cells, at least those with PP-like immunoreactivity, are derived from precursor cells they have in common with other epithelial cells of the midgut.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00217318
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  • 32
    Electronic Resource
    Electronic Resource
    Mitotic activity of prolactin cells in the pituitary glands of male and female rats of different ages (1984)
    Springer
    Cell & tissue research 235 (1984), S. 497-502 
    Details
    ISSN: 1432-0878
    Keywords: Prolactin cell ; Mitosis ; Sex difference ; Aging ; Immunohistochemistry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary The anterior pituitary of colchicine-pretreated male and female rats from 20 days to 12 months of age was stained immunohistochemically with anti-rat prolactin serum. Immunoreactive mitotic cells were identified in all groups of rats. In adult female rats the mitotic index of prolactin cells was higher at oestrus than at other stages of the oestrus cycle and than that in male rats of comparable ages. If adult female rats were ovariectomized on the second day of dioestrus or on the day of proestrus, the mitotic indices at presumptive oestrus were less than those in sham-operated controls at oestrus. Estrogen administration to ovariectomized rats significantly elevated the mitotic index of prolactin cells at 48 h after the treatment. The mitotic indices of prolactin cells in female rats reached a peak at 60 days of age, and then decreased with age. In male rats the mitotic indices showed a steady decrease from the value at 20 days of age. A sex difference in the mitotic indices of prolactin cells was noted from 60 days to 12 months of age. The present results clearly demonstrate that differentiated prolactin cells can undergo mitosis and that a sex difference in the mitotic activity of prolactin cells is present during adult life.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00226945
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  • 33
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    Electronic Resource
    Immunohistochemical demonstration of serotonin-containing nerve fibers in the hypothalamus of the monkey, Macaca fuscata (1984)
    Springer
    Cell & tissue research 236 (1984), S. 495-503 
    Details
    ISSN: 1432-0878
    Keywords: Hypothalamus ; Serotonin ; Neuroendocrine regulation ; Monkey (Macaca fuscata) ; Immunohistochemistry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary The distributional pattern of serotonin-containing nerve fibers in the hypothalamus of the monkey (Macaca fuscata) was analyzed with the use of the peroxidaseantiperoxidase method in conjunction with a highly sensitive and specific anti-serotonin serum. The highest concentrations of serotonin-immunoreactive varicose fibers were found in the nucleus praeopticus medialis, nucleus ventromedialis hypothalami, and the complex of mammillary nuclei (nucleus praemamillaris, supramamillaris, mamillaris medialis et lateralis). However, the nucleus suprachiasmaticus, where numerous serotoninergic fibers have been reported to occur in the rat, appeared to be almost devoid of these fibers. The infundibular stalk, and the intermediate and posterior lobes of the pituitary contained considerable numbers of immunoreactive fibers. The present study provides a morphological basis for possible clarification of the influence of serotoninergic projections on various neuroendocrine mechanisms in primates. Furthermore, an attempt was made to clarify the differences and similarities concerning the distributional patterns of serotoninergic nerve fibers within the monkey hypothalamus in contrast to the rat hypothalamus.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00217216
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  • 34
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    Sustentacular cells in the fetal human adrenal medulla are immunoreactive with antibodies to brain S-100 protein (1984)
    Springer
    Cell & tissue research 236 (1984), S. 733-735 
    Details
    ISSN: 1432-0878
    Keywords: S-100 protein ; Adrenal medulla ; Sustentacular cells ; Human fetus ; Immunohistochemistry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary Adrenal glands of human fetuses were investigated by means of an immunohistochemical method with the use of an anti-S-100 serum. S-100-immunoreactivity was recognized in sustentacular cells located among the chromaffin cells. A characteristic circular arrangement of the immunostained cells was found in the central region of the adrenal glands. It surrounded aggregations of non-argyrophilic, small, round cells, which were identified as the remaining sympathoblasts (primitive sympathetic cells).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00217246
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  • 35
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    Electronic Resource
    Catecholamine-synthesizing enzymes in paraganglia of aged Fischer-344 rats (1984)
    Springer
    Cell & tissue research 238 (1984), S. 217-220 
    Details
    ISSN: 1432-0878
    Keywords: Immunohistochemistry ; Paraganglia ; Aging ; Catecholamines ; Catecholamine-synthesizing enzymes
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary The catecholamine-synthesizing enzymes, tyrosine hydroxylase, dopamine-β-hydroxylase and phenylethanolamine-N-methyltransferase were examined by immunohistochemistry in hypertrophied paraganglia of aged male Fischer-344 rats. All paraganglionic cells reacted with antibodies against tyrosine hydroxylase. Dopamine β-hydroxylase was identified in most paraganglionic cells, indicating that they synthesized norepinephrine. A variable number of paraganglia were positive for phenylethanolamine-N-methyltransferase, which suggested that they synthesized epinephrine. The formaldehyde-induced fluorescence method demonstrated greenish-yellow fluorescence or yellowish-brown fluorescence. The intensity of the fluorescence was in the same range as in adrenal medullary cells. The observations indicate that paraganglia are capable of synthesizing epinephrine.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00217291
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  • 36
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    Electronic Resource
    Monoclonal antibodies against spermatozoa of the common carp (Cyprinus carpio L.) (1984)
    Springer
    Cell & tissue research 236 (1984), S. 99-105 
    Details
    ISSN: 1432-0878
    Keywords: Monoclonal antibodies ; Spermatozoa ; Surface antigens ; Reproductive organs ; Immunohistochemistry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary Eleven monoclonal antibodies that recognize membrane determinants on spermatozoa of the carp Cyprinus carpio L. have been produced. Indirect immunofluorescence revealed that these determinants are uniformly distributed on the surface of head and midpiece. Most of them are also present on the outer membrane of precursor sperm cells. Although none of the monoclonal antibodies reacted with carp somatic tissue, five monoclonal antibodies were positive for surface membrane determinants of oogonia and early prophase oocytes in carp ovary. Preliminary analysis of the testis and ovary of three other species of fish showed that some carp determinants are shared with germ cells from Barbus conchonius, Clarias lazera, or Salmo gairdneri.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00216518
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  • 37
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    Electronic Resource
    Purification and immunohistology of a glycoprotein secreted from the rabbit uterus before implantation (1984)
    Springer
    Cell & tissue research 237 (1984), S. 155-160 
    Details
    ISSN: 1432-0878
    Keywords: Uterine epithelium ; Uterine proteins ; β-Glycoprotein ; Immunohistochemistry ; Rabbit
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary Two antigens of the β-glycoprotein fraction from rabbit uterine secretion of the seventh day post coitum were purified firstly by gel filtration on Sephadex G 150, then either by ion exchange chromatography on DEAE Sephacel or chromatofocusing on PBE 94. By the use of a specific antiserum, raised in female sheep, two antigens with α 2- and β 2-mobility in agar gel electrophoresis could be demonstrated. Immunohistochemical staining of the uterine epithelium at the seventh and eighth day post coitum showed the antigens to be localized in a ciliated cell type of conspicuous shape, which is supposed to be the site of synthesis. Stain accumulated mainly in the apical part of the cell, but there were also small deposits around the nucleus.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00229211
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  • 38
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    Electronic Resource
    The auricular myocardiocytes of the heart constitute an endocrine organ characterization of a porcine cardiac peptide hormone, cardiodilatin-126 (1984)
    Springer
    Cell & tissue research 238 (1984), S. 425-430 
    Details
    ISSN: 1432-0878
    Keywords: Heart, atrium ; Myoendocrine cells ; Cardiodilatin ; Peptide hormone ; Immunohistochemistry ; Pig
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary A peptide hormone was extracted from the porcine right atrium following a bioassay for differential vaso-relaxant effects on smooth muscle strips from aorta and renal and inferior mesenteric arteries. The isolation procedure included several steps of gel-permeation and ion-exchange chromatography, and high performance liquid chromatography. During the isolation procedure, other peptides of smaller molecular weight were also found, which, in relation to cardiodilatin-126 (CDD-126), are shorter at their N-terminal. Among these, CDD-88 has also been isolated and characterizied, and has been established as a prominent member of the cardiac hormone family. The N-terminal and C-terminal segments of the 126 amino acid-containing molecule were synthesized and used to raise region-specific antibodies. The natural peptide was then localized within myoendocrine cells of the right atrium where specific atrial granules are located. Renal effects of cardiodilation were studied in conscious dogs and showed strong diuretic and natriuretic activities. According to our functional studies, cardiodilatin-126 and cardiodilatin-88 possess qualities of a significant hormone family regarding the regulation of extracellular fluid volume and blood pressure.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00219856
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    Charge-Transfer-Komplexe von Tetrathiafulvalen (TTF) mit 1,2,5-Thiadiazolchinonen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1940-1953 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Charge-Transfer Complexes of Tetrathiafulvalene (TTF) with 1,2,5-Thiadiazolequinones1)The syntheses and the X-ray structure analyses of the charge-transfer complexes of tetrathiafulvalene (TTF) with naphtho[2,3-c][1,2,5]thiadiazole-4,9-dione (1 : 2) (2) and benzol[1,2-c: 4,5-c′]-bis[1,2,5]thiadiazole-4,8-dione (1 : 1) (4) are reported. In their crystal structures both compounds are built up by mixed columnar stacks of donors and acceptors, forming a characteristic packing motive for organic D-A complexes with properties of an electrical insulator.
    Notes: Es wird über die Synthese und die Einkristallröntgenstrukturanalysen der Charge-Transfer-Komplexe von Tetrathiafulvalen mit Naphtho[2,3-c][1,2,5]thiadiazol-4,9-dion (1 : 2) (2) und Benzo-[1,2-c: 4,5-c′]bis[1,2,5]thiadiazol-4,8-dion (1 : 1) (4) berichtet. Beide Verbindungen weisen in ihrer Kristallstruktur aus Donoren und Acceptoren gemischte kolumnare Stapel auf, ein charakteristisches Packungsmotiv organischer D-A-Komplexe mit elektrischen Isolatoreigenschaften.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170523
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    Notizen. Die Erzeugung von Nitrosylsalzen in wasserfreien organischen Medien (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1973-1976 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Generation of Nitrosyl Salts in Dry Organic MediaTrimethylsilyl halides (CH3)3SiX (2a - c, X = Cl, Br, I) are sufficiently electrophilic to cleave, in an equilibrium reaction, alkyl nitrites O = NOR (1a, b, R = i-C5H11, C2H5) with formation of O = NX (3a - c) and (CH3)3SiOR (4a, b). This reaction serves as a convenient in-situ-method to generate nitrosyl compounds NOX in chlorinated hydrocarbons as inert organic media.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170526
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  • 41
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    Iminoborane beim thermischen Zerfall der Dialkylazidoborane (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1954-1964 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Iminoboranes from the Thermal Decomposition of DialkylazidoboranesIminoboranes RB = NR (1a - f) are formed by the thermal decomposition of azidoboranes R2BN3 (5a - f) in the gas phase or in solution. At low temperature, the iminoboranes 1b, d, e (R = iPr, iBu, sBu) can be trapped from the gas phase. They are characterized and brought to reaction as isolated species. Without other reactands, the iminoboranes dimerize or trimerize to form the cyclic products 2 or 3, respectively, or polymerize to the wax-like solids 4. Produced in solution below 100 °C, the iminoboranes are azidoborated by the educts 5 to give the (azidoboryl)amines 6 which are transformed into the borazines 3 at 160 - 180 °C. Iminoboranes undergo an ethyloboration with BEt3, a cycloaddition with PhN3, and in the absence of the strongly reactive R2BN3 a concurring cycloaddition and azidosilation with Me3SiN3 with formation of 7 - 10, respectively.
    Notes: Iminoborane RB = NR (1a - f) entstehen beim thermischen Zerfall von Azidoboranen R2BN3 (5a - f) in der Gasphase oder in Lösung. Die aus der Gasphase abgeschiedenen Produkte 1b, d, e (R = iPr, iBu, sBu) lassen sich bei tiefer Temperatur isolieren, charakterisieren und isoliert umsetzen. Mit sich selbst reagieren die in der Gasphase ergzeugten Iminoborane 1a - f unter Cyclodi-oder -trimerisierung oder unter Polymerisierung zu Produkten von Typ 2, 3 bzw. 4. In Lösung unterhalb 100 °C erzeugt, werden die Iminoborane von den Edukten 5 zu Produkten 6 azidoboriert; diese lassen sich bei 160 - 180 °C in Borazine 3 überführen. Iminoborane erfahren durch BEt3 eine Ethyloborierung zu 7, mit PhN3 eine Cycloaddition zu 8 und mit Me3SiN3 nebeneinander eine Cycloaddition zu 9 und eine Azidosilierung zu 10, sofern nicht das Edukt R2BN3 zugegen ist, das dem Azid Me3SiN3 in der Reaktivität gegenüber 1 überlegen ist.
    Additional Material: 6 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170524
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    Azodesilylierung  -  eine neue aprotische Diazotierungstechnik (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1965-1972 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Azodesilylation - a Novel Aprotic Diazotization TechniqueNitrosyl compounds NOA (4a - e, A = Cl, Br, BF4, CF3SO3, I) - generated partially in situ from O = N - OR/(CH3)3SiA (7a, b, R = i-C5H11, C2H5/8a, b, e, A = Cl, Br, I) - react in aprotic organic media with N,N-bissilylated organylamines RN[Si(CH3)3]2 (3b, R = C6H5; 15, R = CH3) under generation of diazonium systems R - N2+ A- and formation of non-nucleophilic hexamethyldisiloxane (6b). This method represents the first nucleophile excluding diazotization technique on the basis of three-coordinated nitrogen and is termed „azodesilylation“.
    Notes: Nitrosylverbindungen NOA (4a - e, A = Cl, Br, BF4, CF3SO3, I) - teilweise in situ hergestellt aus O = N - OR/(CH3)3SiA (7a, b, R = i-C5H11, C2H5/8a, b, e, A = Cl, Br, I) - reagieren mit N,N-bissilylierten Organylaminen RN[Si(CH3)3]2 (3b, R = C6H5; 15, R = CH3) in aprotischen organischen Medien unter Bildung von Diazonium-Systemen R - N2+ A- und nicht-nucleophilem Hexamethyldisiloxan (6b). Diese Methode repräsentiert die erste, Nucleophile ausschließende Diazotierungstechnik auf der Basis von 3fach koordiniertem Stickstoff und wird als „Azodesilylierung“ bezeichnet.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170525
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    Acid-catalyzed Cyclization of the Ene-Product Derived from α-Pinene and PTAD (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1977-1979 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Säurekatalysierte Cyclisierung des En-Produkts aus α-Pinen und PTADAluminiumchlorid-katalysierte Reaktion des En-Produkts 2 aus 4-Phenyl-4H-1,2,4-triazol-3,5-dion (PTAD) und α-Pinen (1), des 1-(6,6-Dimelthyl-2-methylenbicyclo[3.1.1]hept-3-yl)-4-phenyl-1,2,4-triazolidin-3,5-dions, ergab 3,8,8-Trimelthyl-N-phenyl-4,5-diazatricyclo[4.2.1.03,7]nonan-4,5-dicarboxamid (6) in 78% Ausbeute. Auch Bortrifluorid-etherat, trockener Chlorwasserstoff und p-Toluolsulfonsäure katalysieren die Cyclisierung von 2 zu 6, aber nicht in diesem Maße. Der Mechanismus der Cyclisierung wird über eine Gerüstumlagerung der Carbenium-Ionen-Zwischenstufen gedeutet.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170527
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  • 44
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    Kettenverlängerung bei Tetrafluor-1,2-ethandisulfenyldichlorid durch Reaktion mit Wasserstoffperoxid (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1980-1981 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chain Lengthening of Tetrafluoro-1,2-ethanedisulfenyl Dichloride by the Reaction with Hydrogen PeroxideThe reaction of the little compound ClSCF2CF2SCl (1) with aqueous H2O2 results in the formation of ClS2CF2CF2SSCF2CF2SO2Cl(2), which is characterized on the basis of 19F NMR, mass, IR, and Raman spectroscopy.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170528
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  • 45
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    Fluorierungen von Adamantanderivaten mit Sauerstoffdifluorid (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1982-1986 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Fluorination of Adamantane Derivatives with Oxygen DifluorideFluorination of adamantane and adamantane derivatives 1 with OF2 in the absence of an HF-trap gives fluoroadamantanes 2 and adamantanols 3 in varying amounts. Increasing yields of 2 are obtained in the presence of Na2CO3 as an HF-trap. In addition, the fluorooxahomoadamantanes 4b and e are formed in this reaction. The fluorination of adamantanone (5) with OF2 leads to analogous products.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170529
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  • 46
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    Photoelectron Spectra of Some Reduction Products of [2.2]Paracyclophane (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1987-1990 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Photoelektronenspektren einiger Reduktionsprodukte von [2.2]ParacyclophanAnhand des He(I)-Photoelektronen(PE)-Spektrums von 2,3′,5,6′-Tetrahydro[2.2]paracyclophan (2) wird gezeigt, daß die Through-Bond-Wechselwirkung zwischen den Sechsringen klein, innerhalb der Cyclohexadienringe aber groß ist. Über die PE-Spektren der weiteren Hydrierungsprodukte 3 und 4 wird berichtet.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170530
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  • 47
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    Synthesen mit Cyclobutadienen, 5. 5,5,6,6-Tetracyan-5,6-dihydrodewarbenzol/3,3,4,4-Tetracyan-3,4-dihydrobenzavalen - ein neues äquilibrierendes System (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1991-1993 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Syntheses with Cyclobutadienes, 51). 5,5,6,6-Tetracyano-5,6-dihydro-Dewar benzene/3,3,4,4-Tetracyano-3,4-dihydrobenzvalene - a Novel Equilibrating SystemThe cyclobutadiene 3 reacts with tetracyanoethylene to give a 1 : 1-mixture of the dihydro-Dewar benzene 5 and the dihydrobenzvalene 6, which can be separated by crystallisation. In deuteriochloroform solution 5 and 6 are in a 1 : 1 equilibrium.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170531
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    Masthead (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984) 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170601
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  • 49
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    Elektronenreiche Heterocyclen als Donorgruppen in Fluoreszenzfarbstoffen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 2275-2286 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Electron Rich Heterocycles as Donor Groups in Fluorescent DyesThe synthesis of N-methylphthalimides substituted with the donor groups pyrazole, triazole, benzotriazole, and naphthotriazole in position 4 is described (17, 18, 14, 12). The substituent constants of these groups are obtained by alkaline hydrolysis of the corresponding phthalimide dyes. Their solvatochromism in absorption and fluorescence gives information about charge distribution in ground- and excited state.
    Notes: Die Darstellung von N-Methylphtalimiden wird beschrieben, die in 4-Stellung die Donorgruppen Pyrazol, Triazol, Benzotriazol und Naphthotriazol tragen (17, 18, 14, 12). über die alkalische Hydrolyse des Imids werden die Substituentenkonstanten der Reste bestimmt. Die Solvatochromie in Absorption und Fluoreszenz gibt Information über die Ladungsverteilung in Grund- und angeregtem Zustand.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170619
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  • 50
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    Aromaten(phosphan)metall-Komplexe, IV. Darstellung von (6-Phosphonio-η5-cyclohexadienyl)-ruthenium(II)-Verbindungen und ihre Umwandlung in dikationische (Benzol)ruthenium(II)-Komplexe [C6H6Ru(PR3′)PR3″]2+ (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 142-151 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Arene(phosphane)metal Complexes, IV1). Synthesis of (6-Phosphonio-η5-cyclohexadienyl)ruthenium(II) Compounds and their Conversion into Dicationic (Benzene)ruthenium(II) Complexes[C6H6Ru(PR3)(PR3′)PR3″]2+The complexes [C6H6RuCl(PR3)PR3′]PF6 (1 - 4) and [C6H6RuCl2(PR3)] (9, 10) react with phosphanes PR3″ in the presence of NH4PF6 to give the (6-phosphonio-η5-cyclohexadienyl)ruthenium(II) compounds [(6-R3″P-η5-C6H6)Ru(PR3)(PR3′)PR3″](PF6)2 (5 - 8 11). Similarly, from [C6H6Ru(CH3CN)3](PF6)2 (12) and PMe3 the complex [(6-Me3P-η5-C6H6)Ru(PMe3)2CH3CN](PF6)2 (13) is formed. The IR and NMR spectra of 5 - 8, 11, and 13 indicate that the phosphonio group is in the exo-position at the sp3 carbon atom of the cyclohexadienyl ligand. Below - 30°C, rotation around the metal-ring bond is so hindered that rigid conformers are detected. Compounds 5 - 8 react with trifluoroacetic acid with elimination of the phosphonio group to yield the PF6 salts of the half-sandwich type complexes [C6H6Ru(PR3)(PR3′)PR3″]2+ (14 - 17).
    Notes: Die Komplexe [C6H6RuCl(PR3)PR3)]PF6 (1 - 4) und [C6H6RuCl2(PR3)] (9, 10) reagieren mit Phosphanen PR3″ in Gegenwart von NH4PF4 zu den (6-Phosphonio-η5-cyclohexadienyl)-ruthenium(II)-Verbindungen [(6-R3″P-η5-C6H6)Ru(PR3)(PR3″](PF6)2 (5 - 8, 11). Aus [C6H6Ru(CH3CN)3](PF6)2 (12) und PMe3 erhält man analog den Komplex (6-Me3P-η5-C6H6)Ru(PMe3)2CH3CN](PF6)2 (13). Die IR- und NMR-Spektren von 5 - 8, 11 und 13 weisen darauf hin, daß sich die Phosphoniogruppierung in der exo-Position am sp3-C-Atom des Cyclohexadienylliganden befindet. Unterhalb - 30°C ist die Rotation um die Metall-Ring-Bindung so stark behindert, daß starre Konformere nachweisbar sind. Die Verbindungen 5 - 8 reagieren mit Trifluoressigsäure unter Abspaltung der Phosphoniogruppe zu den PF6-Salzen der Halbsandwich-Komplexe [C6H6Ru(PR3)(PR3′)PR3″]2+ (14 - 17).
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170111
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    Aromaten(phosphan)metall-Komplexe, VI. Synthese von [(RC6H5)OsI(PMe3)2PF6 aus (exo-6-RC6H6)OsI(PMe3)2: Ein Beitrag zum Mechanismus der Aromatisierung substituierter Cyclohexadienylliganden durch „endo-H-Abstraktion“ (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 161-171 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Arene(phosphane)metal Complexes, VI1). Synthesis of [(RC6H5)OsI(PMe3)2]PF6 from (exo-6-RC6H6)OsI(PMe3)2: A contribution to the Mechanism of Aromatization of Substituted Cyclohexadienyl Ligands by „endo-H Abstraction“The compounds (exo-6-RC6H6)OsI(PMe3)2 (2 - 5, 7) react smoothly with [CPh3]PF6 in acetone to give the (arene)osmium(II) complexes [(RC6H5)OsI(PMe3)2]PF6 (8 - 12) in quantitative yield. The hydride elimination proceeds via two (cyclohexadienyl)hydridoosmium(IV) intermediates (13 and 14, 15, respectively) which can be prepared from 2, 5, 6 (R = CH3, n-C4H9, t-C4H9) and CF3CO2H/NH4PF6. The (cyclohexadienyl)hydrido complexes [(RC6H6)Os(H)I(PMe3)2]+ undergo an intramolecular isomerization which leads to a cation possessing a CH2 group in the six-membered ring. This cationic complex or (more probably) the neutral compound (2- or 3-RC6H6)OsI(PMe3)2 formed on deprotonation reacts with [CPh3]+ by abstraction of an exo-hydrogen atom.
    Notes: Die Verbindungen (exo-6-RC6H6)OsI(PMe3)2 (2 - 5, 7) reagieren mit [CPh3]PF6 in Aceton rasch und quantitativ zu den (Aromaten)osmium(II)-Komplexen [(RC6H5)OsI(PMe3)2]PF6 (8 - 12). Die Hydrid-Eliminierung verläuft über zwei (Cyclohexadienyl)hydridoosmium(IV)-Zwischenstufen (13 bzw. 14, 15), die aus 2, 5, 6 (R = CH3, n-C4H9, t-C4H9) und CF3CO2H/NH4PF6 synthetisiert werden können. Die (Cyclohexadienyl)hydrido-Komplexe [(RC6H6)Os(H)I(PMe3)2]+ gehen eine intramolekulare Isomerisierung ein, wobei ein Kation mit einer CH2-Gruppe im Sechsring entsteht. Dieses Komplexkation oder (wahrscheinlicher) die nach Deprotonierung erhaltene Neutralverbindung (2- bzw. 3-RC6H6)OsI(PMe3)2 reagiert mit [CPh3]+ unter Abstraktion eines exo-H-Atoms.
    Additional Material: 4 Tab.
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    URL: http://dx.doi.org/10.1002/cber.19841170113
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    Aromaten(phosphan)metall-Komplexe, V. Zur Addition von Carbanionen an (Benzol)ruthenium(II)- und -osmium(II)-Komplexe. Kristall- und Molekülstruktur von (exo-6-n-C4H9-η5-C6H6)OsI(PMe3)2 (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 152-160 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Arene(phosphane)metal Complexes, V1). On the Addition of Carbanions to (Benzene)ruthenium(II) and -osmium(II) Complexes. The Crystal and Molecular Structure of (exo-6-n-C4H9-η5-C6H6)OsI(PMe3)2The complex [C6H6RuCl(PMe3)2]PF6 (1) reacts with methyllithium to give a mixture of products that contains (η5-C6H6CH3)RuCH3(PMe3)2 (2) as the main component. From 1 and LiC6H5/LiBr the bromide 3 is primarily formed but the final product is (η5-C6H6C6)H5RuC6H5(PMe3)2 (4). Reaction of [C6H6OsI(PMe3)2]PF6 (5) with organyllithium compounds LiR (R = CH3, C2H5, n-C3H7, n-C4H9, t-C4H9, C6H5) yields the complexes (η5-C6H6R)OsI(PMe3)2 (6 - 11). 31P NMR spectra of 6 - 11 indicate restricted rotation at low temperatures around the metal-ring axis. According to X-ray structure analysis of 9 (R = n-C4H9) the cyclohexadienyl ring possesses an envelope conformation. The n-butyl group occupies the exo-position at the sp3-C atom.
    Notes: Der Komplex [C6H6RuCl(PMe3)2]PF6 (1) reagiert mit Methyllithium zu einem Produktgemisch, welches (η5-C6H6CH3)RuCH3(PMe3)2 (2) als Hauptkomponente enthält. Aus 1 und LiC6H5/LiBr entsteht über 3 bei längeren Reaktionszeiten (η5-C6H6C6H5)RuC6H5(PMe3)2 (4). Die Umsetzung von [C6H6OsI(PMe3)2]PF6 (5) mit Organyllithium-Verbindungen LiR (R = CH3, C2H5, n-C3H7, n-C4H9, t-C4H9, C6H5 ergibt die Komplexe (η5-C6H6R)OsI(PMe3)2 (6 - 11), in denen nach den 31P-NMR-Spektren die Rotation um die Metall-Ring-Bindung bei tiefen Temperaturen stark eingeschränkt ist. Die Röntgenstrukturanalyse von 9 (R = n-C4H9) beweist die „Envelope“-Konformation des Cyclohexadienylrings. Die n-Butylgruppe befindet sich in der exo-Position am sp3-C-Atom.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19841170112
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    Radikalionen, 55. Die Einelektronen-Oxidation von Tetrahedran zum Cyclobutadien-Radikalkation (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 172-186 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Radical Ions, 55. The One-Electron Oxidation of Tetrahedrane to Cyclobutadiene Radical CationTetra-tert-butyltetrahedrane, on one-electron oxidation using AlCl3 in CH2Cl2, opens to form tetra-tert-butylcyclobutadiene radical cation, which can also be generated under identical reaction conditions from tetra-tert-butylcyclobutadiene itself. The assignments of the ESR and ENDOR spectra are supported by deutero substitution of one tert-butyl group and by MNDO hypersurfaces for the thermal and for the oxidative structural changes of both C4 skeletons. The feasible formation of a valence isomeric tert-butyl(tri-tert-butylcyclopropenyl)carbene radical cation is discussed.
    Notes: Tetra-tert-butyltetrahedran öffnet sich bei Einelektronen-Oxidation mit AlCl3 in CH2Cl2 zum Tetra-tert-butylcyclobutadien-Radikalkation, das unter gleichen Reaktionsbedingungen auch aus Tetra-tert-butylcyclobutadien erzeugt werden kann. Die Zuordnungen der ESR- und ENDOR-Spektren werden durch Deutero-Substitution einer tert-Butyl-Gruppe sowie durch MNDO-Hyperflächen für die thermischen und oxidativen Strukturänderungen der beiden C4-Gerüste gestützt. Die mögliche Bildung eines valenzisomeren tert-Butyl(tri-tert-butylcyclopropenyl)carben-Radikalkations wird diskutiert.
    Additional Material: 4 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19841170114
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    Saure Komplexone mit Donor-verstärkter Pyridin-Ankergruppe (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 948-954 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Acidic Complexones Bearing Donor-enhancing Pyridine Anchour GroupsThe synthesis, complex stability and -selectivity for alkaline earth metal ions of 2,6-pyridinebis-(methylamine)-N, N, N′, N′-tetraacetic acid (3a) and of their donor-enforced analogues 3b, c are described. The acid dissociation constants and the stability constants of the metal complexes have been measured potentiometrically at 25°C in water of constants ionic strength (μ = 0.1). The stability order is Ca 〉 Mg 〉 Sr 〉 Ba which is analogues to the selectivity of EDTA and comparable aliphatic complexones. The magnitudes of the stability constants of 3a are comparable to those of EDTA, while the donor-enforced analogues 3b, c form less stable complexes with alkaline earth metal ions.
    Notes: Synthese, Komplexstabilität und -selektivität gegenüber Erdalkalimetall-Ionen von 2,6-Pyridinbis(methylamin)-N, N, N′, N′-tetraessigsäure (3a) und ihren Donor-verstäkten Analoga 3b, c werden beschrieben. Die Bestimmung der Dissoziations- und Komplexbildungskonstanten erfolgt potentionmetrisch bei 25°C in Wasser konstanter ionaler Stärke (μ = 0.1). Die Bildungskonstanten der Metallkomplexe nehmen in der Reihenfolge Ca 〉 Mg 〉 Sr 〉 Ba ab und folgen damit der bei EDTA und vergleichbaren aliphatischen Komplexonen vorgefundenen Selektivität. 3a weist mit EDTA vergleichbare hohe Komplexbildungskonstanten auf, während die Donor-verstärkten Analoga 3b, c schwächere Erdalkalimetallkomplexe bilden.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19841170308
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    Darstellung und Röntgenstrukturanalyse des Diels-Alder-Addukts von 4-Phenyl-4H-1,2,4-triazol-3,5-dion an Octavalen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 959-965 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Preparation and X-Ray Structure Analysis of the Diels-Alder Adduct of 4-Phenyl-4H-1,2,4-triazole-3,5-dione with OctavaleneIn the reaction of 4-phenyl-4H-1,2,4-triazole-3,5-dione with octavalene (1) the Diels-Alder adduct 2 is formed. From its X-ray structure analysis the dihedral angle for the bicyclo[1.1.0]butane group, the 2- and 4-positions of which are spanned by four atoms, has been determined to be 122.7°. The bridging bond C1 - C3 has a length of 1.487 Å.
    Notes: Aus Octavalen (1) und 4-Phenyl-4H-1,2,4-triazol-3,5-dion bildet sich das Diels-Alder-Addukt 2. Seine Röntgenstrukturanalyse ergab für das Bicyclo[1.1.0]butan-Gerüst, dessen 2- und 4-Stellung durch vier Atome überbrückt sind, einen Interplanarwinkel von 122.7°. Die Brückenbindung C1 - C3 hat eine Länge von 1.487 Å.
    Additional Material: 3 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19841170310
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    Kondensierte Ringsysteme, XV. Über die Reaktion von α-Chlorsulfoxiden mit Kalium-tert-butylat am Beispiel der Synthese von Oxapropellenen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 966-981 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Condensed Ring Systems, XV. About the Reaction of α-Chloro Sulfoxides with Potassium tert-Butoxide by the Example of the Synthesis of OxapropellenesThe synthesis of dithia- 1a - 3a and oxathiapropellenes 1b - 3b is described. From 1b - 3b the α-chloro sulfoxides 4 - 6 and α-chloro sulfones 4a - 6a are prepared, or which in most cases several stereoisomeric racemates are obtained. The constitution, configuration, and conformation of the α-chloro sulfoxide 4, the main product obtained from 1b, was elucidated by X-ray structure analysis. Only in that way it was possible to deduce the constitutions and configurations of the other stereoisomeric α-chloro sulfoxides 4 - 6 and α-chloro sulfones 4a - 6a, respectively, using 13C NMR spectroscopy. By the reaction of the α-chloro sulfones 4a - 6a with potassium tert-butoxide (Ramberg-Bäcklund reaction) the corresponding oxapropellenes 7 - 9 are obtained only in low yields (〈 10%). Contrary, the α-chloro sulfoxides 4 - 6, und analogous conditions give yields of 80 - 90% (from 4, 6) and 25% (from 5).
    Notes: Es wird die Synthese der Dithia- 1a - 3a und Oxathiapropellene 1b - 3b beschrieben. Aus 1b - 3b werden die α-Chlorsulfoxide 4 - 6 und α-Chlorsulfone 4a - 6a hergestellt, von denen meist mehrere stereoisomere Racemate erhalten werden. Konstitution, Konfiguration und Konformation des Hauptprodukts der aus 1b erhaltenen α-Chlorsulfoxide 4 wurden durch Röntgenstrukturanalyse ermittelt. Erst dadurch wurde es möglich, mit Hilfe der 13C-NMR-Spektroskopie die Konstitutionen und Konfigurationen der anderen stereoisomeren α-Chlorsulfoxide 4 - 6 und α-Chlorsulfone 4a - 6a aufzuklären. Bei der Reaktion der α-Chlorsulfone 4a - 6a mit Kalium-tert-butylat (Ramberg-Bäcklund-Reaktion) erhält man die entsprechenden Oxapropellene 7 - 9 nur in geringer Ausbeute (〈 10%), während die α-Chlorsulfoxide 4 - 6 unter analogen Bedingungen Ausbeuten von 80 - 90% (aus 4, 6) und 25% (aus 5) ergeben.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19841170311
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    Über die Selektivität bei der Umsetzung von Carbokationen mit Nucleophilen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 982-989 
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    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: On the Selectivity of the Reaction of Carbocations with NucleophilesThe problem of the selectivity of the nucleophilic attack on carbocations according to the HSAB-principle is discussed in relation to the solvolysis in ether of 7,7-bis(trifluoromethylsulfonyloxy)-norbornane (2) and 7,7-bis(trifluoromethylsulfonyloxy)-2-norbornene (4) in presence of dimethyl-magnesium, magnesium iodide and methylmagnesium iodide. The nucleophiles and carbocations are arranged according to the hard-soft-scale, so our results can be explained.
    Notes: Das Problem der Selektivität beim nucleophilen Angriff an Carbokationen wird im Rahmen des HSAB-Prinzips am Beispiel der Solvolysen in Ether von 7,7-Bis(trifluormethylsulfonyloxy)norbornan (2) und 7,7-Bis(trifluormethylsulfonyloxy)-2-norbornen (4) in Anwesenheit von Dimethylmagnesium, Magnesiumiodid und Methylmagnesiumiodid erörtert. Die Nucleophile und die als Zwischenstufen auftretenden Carbokationen werden auf der Hart-weich-Skala eingeordnet, wobei die Ergebnisse erklärt werden können.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170312
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    Dichloropalladium(II)-Komplexe mit α-Aminosäuren, α-Aminosäureestern, Dipeptiden und Dipeptidestern (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1003-1012 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Dichloropalladium(II) Complexes with α-Amino Acids, α-Amino Acid Esters, Dipeptides, and Dipeptide EstersA series of trans-dichloropalladium(II) complexes Cl2PdL2 (L = α-amino acid, α-amino acid ester, dipeptide, dipeptide esters) and cis-Cl2Pd(histidine) has been prepared and spectroscopically characterized. The X-ray structure of trans-Cl2Pd(GlyOEt)2 (3b) has been determined.
    Notes: Eine Reihe von trans-Dichloropalladium(II)-Komplexen Cl2PdL2 mit (L = α-Aminosäure, α-Aminosäureester, Dipeptid, Dipeptidester) sowie cis-Cl2Pd(Histidin) wurde dargestellt und spektroskopisch charakterisiert. Die Röntgenstruktur von trans-Cl2Pd(GlyOEt)2 (3b) wurde bestimmt.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19841170314
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    Der Nachweis eines Radikalketten-Mechanismus für die Knabe-Reaktion von 1,2-Dihydro-2-methylpapaverin (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1436-1454 
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    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Evidence for a Radical Chain Mechanism for the Knabe Reaction of 1,2-Dihydro-2-methylpapaverineA free radical chain mechanism is proposed for the Knabe reaction and the accompanying elimination reaction on account of their nonintegral reaction order and of successful inhibition experiments. 3,4-Dimethoxybenzyl radicals are the chain carrying species. Battersby's synthesis of N-methylpavine (19) from 1,2-dihydro-2-methylpapaverine (9) is dependent on the presence of formic acid as radical chain inhibitor. In the presence of inhibitors 1-benzyl-1,4-dihydro-2-methyl-isoquinolinium ions like 10 are persistent species whose chemistry can now be investigated.
    Notes: Die Knabe-Reaktion von 1,2-Dihydro-2-methylpapaverin (9) und die begleitende Eliminierungsreaktion wurden durch ihre gebrochene Reaktionsordnung und durch die Möglichkeit der Inhibition als Radikalkettenreaktionen erkannt, deren kettentragendes Radikal das 3,4-Dimethoxybenzylradikal ist. Die Synthese von N-Methylpavin (19) aus 1,2-Dihydro-2-methylpapaverin (9) ist an die Anwesenheit von Ameisensäure als Inhibitor der Radikalketten gebunden. Durch Zusatz von Inhibitoren können nun Immoniumionen 10 und analoge Verbindungen stabilisiert und ihre Chemie untersucht werden.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19841170414
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    Azobrücken aus Azinen, III. Unerwartete Bildung einer Verbindung mit parallelen C=C- und N=N-Bindungen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1455-1464 
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    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Azo Bridges from Azines, III. Unexpected Formation of a Compounds with Parallel C=C and N=N Bonds2)Dialdehyde 5 reacts with hydrazine at pH 〉 7 to form the trimeric azine 6Tr, at pH 〈 4, however, to yield unexpectedly 8, which contains parallel C=C and N=N bonds in close proximity. The complex reaction is clarified. 8 is characterized by structure proving reactions and its spectroscopic data.
    Notes: Der Dialdehyd 5 reagiert mit Hydrazin bei pH 〉 7 zu dem trimeren Azin 6Tr, bei pH 〈 4 unerwartet zu 8, das parallel benachbarte C=C- und N=N-Bindungen besitzt. Der komplexe Reaktionsverlauf wird aufgeklärt. 8 wird durch struktursichernde Reaktionen und spektroskopische Daten charakterisiert.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19841170415
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    Azobrücken aus Azinen, IV. Intramolekulare [2 + 2]-Photocycloaddition zwischen parallelen C=C- und N=N-Bindungen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1465-1475 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Azo Bridges from Azines, IV1). Intramolecular [2 + 2] Photocycloaddition of Parallel C=C and N=N BondsThe parallel C=C and N=N bonds in the rigid molecules 1 - 10 photocyclize nearly quantitatively, forming 1,2-diazetidines 11 - 20. Their structure is confirmed by spectroscopic methods and for 13 by X-ray analysis. Radiation induced denitrogenation, the normal reaction for similar compounds without neighbouring C=C bonds, is suppressed even with the sensitive derivatives of 2,3-diazabicyclo[2.2.1]heptene. Photocyclization of 6, carrying two neighbouring C=C bonds, includes only the norbornene bond.
    Notes: In den starren Molekülen 1 - 10 reagieren die benachbarten parallelen C=C- und N=N-Bindungen nahezu quantitativ unter Photocyclisierung zu den 1,2-Diazetidinen 11 - 20, deren Struktur spektroskopisch und für 13 durch Kristallstrukturanalyse bewiesen wird. Die in Abwesenheit der C=C-Bindung beobachtete Photo-Denitrogenierung unterbleibt selbst bei den empfindlichen Derivaten des 2,3-Diazabicyclo[2.2.1]heptens. Photocyclisierung von 6 mit zwei zur N=N-Bindung benachbarten C=C-Bindungen tritt nur mit der Norbornendoppelbindung ein.
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    URL: http://dx.doi.org/10.1002/cber.19841170416
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    Aminosäuren, 2. N-Acetyl-α,β-didehydro-α-aminosäureester durch Stickstoffabspaltung aus α-Azidocarbonsäureestern mit Rhenium-Katalysatoren (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1497-1512 
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    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Amino Acids, 21,2). N-Acetyl α,β-Didehydro α-Amino Acid Esters from α-Azidocarboxylic Acid Esters and Acetic Anhydride by Nitrogen Elimination with Rhenium Catalystsα-Azidocarboxylic acid esters 2 react with acetic anhydride in presence of catalytic amounts of rhenium heptasulfide and - if necessary - by addition of hydrochloric acid to give N-acetyl 3 or/and N,N-diacetyl-α,β-didehydro-α-amino acids esters 4 in very good yields. Exclusively monoacetylated products 3 are formed if water ist added before work up.
    Notes: Beim Erwärmen von α-Azidocarbonsäureestern 2 in Acetanhydrid/Essigsäure in Gegenwart katalytischer Mengen Rheniumheptasulfid und gegebenenfalls unter Zugabe von Chlorwasserstoff entstehen in sehr guten Ausbeuten N-Acetyl- 3 und/oder N,N-Diacetyl-α-β-didehydro-α-amino-säureester 4. Durch Zugabe von Wasser vor der Aufarbeitung erfolgt partielle Deacetylierung unter ausschließlicher Bildung der N-Monoacetylverbindungen 3.
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    URL: http://dx.doi.org/10.1002/cber.19841170419
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    Aminosäuren, 3. N-Acetylierte α-β-Didehydro-α-aminosäure-Derivate durch Stickstoffabspaltung aus α-Azidocarbonsäureamiden und α-Azido-ω-aminocarbonsäurelactamen mit Rhenium-Katalysatoren (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1513-1522 
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    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Amino Acids, 31). N-Acetylated α-β-Didehydro α-Amino Acid Derivatives by Nitrogen Elimination from α-Azido-carboxylic Acid Amides and α-Azido-ω-aminocarboxylic Acid Lactams with Rhenium Catalystsα-Azidocarboxylic acid amides 2 and α-azido-ω-aminocarboxylic acid lactams 6, respectively, react with acetic anhydride in the presence of rhenium catalysts by nitrogen eliminations to give N-acetyl- 7 and N,N-diacetyl-α,β-didehydro-α-amino acid amides 8, α-acetylamino- 11 and α-diacetylamino-α,β-didehydro-ω-aminocarboxylic acid lactams 12, respectively. Reactions of the educts 6c, d - with a ring size 7 or 8 - additionally lead to the oxazoloazepine 14c and the oxazoloazocine 14d, respectively.
    Notes: Bei der Umsetzung von α-Azidocarbonsäureamiden 2 mit Acetanhydrid in Gegenwart von Rheniumkatalysatoren entstehen unter Stickstoffabspaltung N-Acetyl- 7 und N,N-Diacetyl-α,β-didehydro-α-aminosäureamide 8, bei der von α-Azido-ω-aminocarbonsäurelactamen 6 α-Acetyl-amino- 11 und α-Diacetylamino-α,β-didehydro-ω-aminocarbonsäurelactamen 12, wobei sich aus den Verbindungen 6c, d, mit der Ringgliederzahl 7 bzw. 8 außerdem noch das Oxazoloazepin 14c bzw. das Oxazoloazocin 14d bilden.
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    Beiträge zur Chemie des Phosphors, 1311,2). Synthese und Eigenschaften der Methylendiphosphirane (t-BuP)2C = CR2 (R = H, Me, 4-ClC6H4) (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1542-1550 
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    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Contributions to the Chemistry of Phosphorus, 131. Synthesis and Properties of the Methylenediphosphiranes (t-BuP)2)C = CR2 (R = H, Me, 4-ClC6H4)The first methylenediphosphiranes (diphosphamethylenecyclopropanes) (t-BuP)2C = CH2 (1), (t-BuP)2C = CMe2 (2), and (t-BuP)2C = C(4-ClC6H4)2 (3) were synthesized by [2 + 1] cyclocondensation of K(t-Bu)P - P(t-Bu)K with the corresponding 1,1-dichloroolefins. The homocyclophosphanes (t-BuP)n (n = 4,3) and in the case of 1 mainly H(t-Bu)P - P(t-Bu)H are formed as by-products. The three-membered heterocycles 2 and 3 could be purely isolated as surprisingly stable compounds. According to an X-ray single-crystal analysis 3 possesses approximately C2 symmetry and exhibits one of the smallest bonding angles ψ (P - P - C) = 52.4° on a phosphorus atom experimentally proved so far. Along [100] there are canals filled with disordered n-pentane molecules.
    Notes: Die ersten Methylendiphosphirane (Diphosphamethylencyclopropane) (t-BuP)2C = CH2 (1), (t-BuP)2C = CMe2 (2) und (t-BuP)2C = C(4-ClC6H4)2 (3) wurden durch [2 + 1]-Cyclokondensation von K(t-Bu)P - P(t-Bu)K mit den entsprechenden 1,1-Dichlorolefinen synthetisiert. Als Nebenprodukte entstehen die Homocyclophosphane (t-BuP)n (n = 4,3) und im Fall von 1 vor allem H(t-Bu)P - P(t-Bu)H. Die Dreiringheterocyclen 2 und 3 konnten als thermisch überraschend beständige Verbindungen in reiner Form isoliert werden. 3 besitzt nach der Röntgenstrukturanalyse annähernd die Symmetrie C2 und enthält mit ψ (P - P - C) = 52.4° einen der kleinsten experimentell gesicherten Bindungswinkel am Phosphor. Längs [100] liegen fehlgeordnet mit n-Pentan gefüllte Kanäle vor.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19841170422
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    Amination, III. Trimethylsilanol as Leaving Group, V. Silylation - Amination of Hydroxy N-Heterocycles (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1523-1541 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Aminierung, III. Trimethylsilanol als austretende Gruppe, V. Silylierung-Aminierung von Hydroxy-N-heterocyclenDurch Silylierung-Aminierung lassen sich Hydroxy-N-heterocyclen (z. B. 18, 21, 26 u. a.) bequem in einer Einstufen-Eintopfreaktion aminieren (→ 20, 23 - 25 etc.). Aromatische Hydroxy-N-heterocyclen werden durch Silylierung in aktivierte und lipophile Zwischenprodukte vom Typ 3, 8 umgewandelt, die sich in situ mit Ammoniak, primären oder sekundären Aminen zu den entsprechenden mono-, bis- und tris-aminierten Produkten (5, 10) umsetzen. Die Additions-Eliminierungsreaktion von Aminen an O-silylierte Heterocyclen ist Lewissäure-katalysiert und verläuft gewöhnlich in hohen Ausbeuten, falls die austretende Gruppe Trimethylsilanol in situ durch überschüssiges Silylierungsmittel in Hexamethyldisiloxan umgewandelt wird. Anwendungsbreite und Grenzen dieser einfachen Methode werden diskutiert.
    Notes: Hydroxy N-heterocycles such as 18, 21, 26, and others are efficiently aminated in a one-step/one-pot procedure by silylation-amination to give 20, 23 - 25 etc. Silylation converts aromatic hydroxy N-heterocycles into activated and lipophilic intermediates of type 3, 8 which react in situ with ammonia, primary or secondary amines to form the corresponding mono-, bis- or tris-aminated products (5, 10). This addition-elimination of amines to O-silylated heterocycles in Lewis acid-catalyzed and proceeds usually in high yields if the leaving group trimethylsilanol is converted in situ by excess silylated agent into hexamethyldisiloxane. Scope and limitations of this simple procedure are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170421
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    Benzonitril als 6-Elektronen-Donor-Ligand: Die Cluster Fe3(CO)9(μ3(η2)-NCC6H5) und Fe4(CO)12(μ4(η2)-NCC6H5) (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1572-1582 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Benzonitrile as a 6-Electron Donor Ligand: The Clusters Fe3(CO)9(μ3(η2)-NCC6H5) and Fe4(CO)12(μ4(η2)-NCC6H5)The reaction of Fe3(CO)12 with benzonitrile in the presence of hydrogen leads to the benzonitrile complexes Fe3(CO)9(μ3(η2)-NCC6H5) (1a) and Fe4(CO)12(μ4(η2)-NCC6H5) (2). Their structures were determined crystallographically. The benzonitrile ligand is coordinated to the iron atoms formally via on „s̰-bond“ and two „π-bonds“ in 1a, and via three s̰-bonds and one π-bond in 2.
    Notes: Die Reaktion von Fe3(CO)12 mit Benzonitril in Anwesenheit von Wasserstoff führt zu den beiden Benzonitril-Komplexen Fe3(CO)9(μ3(μ2)-NCC6H5) (1a) und Fe4(CO)12(μ4(η2)-NCC6H5) (2). Ihre Strukturen wurden kristallographisch aufgeklärt. Der Benzonitril-Ligand ist in 1a formal über eine „s̰-Bindung“ und zwei „π-Bindungen“, in 2 über drei s̰-Bindungen und eine π-Bindung an die Eisenatome koordiniert.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170425
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    Kernspin-Kopplungskonstanten mit Platin-195 als Kriterien für die Konfigurations-Bestimmung platin-organischer Verbindungen des zweiwertigen Platins (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1606-1619 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Spin-Spin Coupling Constants by Platinium-195 as Criteria for a Configuration Determination in Platinum Organic CompoundsThe platinum organic compounds [Pt(η4-1,5-cyclooctadiene)(XC6H4)2] and cis-[Pt(P(n-Bu)3)2-(XC6H4)2] (X = H, 4-CH3, 4-(CH3)3C, 4-(CH3)2N, 3-F, 4-F, 4-CH3O, 4-CF3; 3a - 4, cis-4a - h) as well as trans-[Pt(P(n-Bu)3)2(4-CH3OC6H4)2] (trans-4g) and trans-[Pt(P(n-Bu)3)2(4-CF3C6H4)2] (trans-4h) have been studied by 31P-, 13C-, and 1H NMR spectroscopy. The coupling constants 1J[195Pt, 31P], nJ[195Pt, 13C], nJ[195Pt, H], and 2J[31P, 13C] show a clear correlation to the ligand configuration at the dsp2-hybridized platinum and can therefore be used as basis for configuration determination.
    Notes: Die platin-organischen Verbindungen [Pt(η4-1,5-cyclooctadien)(XC6H4)2] und cis-[Pt(P(n-Bu)3)2-(XC6H4)] (X = H, 4-CH3, 4-(CH3)3C, 4-(CH3)2N, 3-F, 4-F, 4-CH3O, 4-CF3; 3a - h, cis-4a - h) sowie trans-[Pt(P(n-Bu)3)2(4-CH3OC6H4)2] (trans-4g) und trans-[Pt(P(n-Bu)3)2(4-CF3C6H4)2] (trans-4h) wurden 31P-, 13C- und 1-NMR-spektroskopisch untersucht. Die Kopplungskonstanten 1J[195Pt, 31P], nJ[195Pt, 13C], nJ[195Pt, H] und 2J[31P, 13C] zeigen eine eindeutige Abhängigkeit von der Konfiguration der Liganden am dsp2-hybridisierten Platin; sie können daher zur sicheren Konfigurations-Bestimmung verwendet werden.
    Additional Material: 8 Tab.
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    URL: http://dx.doi.org/10.1002/cber.19841170429
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    Zur Struktur von N-Methylencarbonsäureamiden: Röntgenstrukturergebnisse, spektroskopische Untersuchung und quantenmechanische Berechnungen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1597-1605 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: On the Structure of N-Methylenecarboxamides: X-Ray Data, Spectroscopy, and Quantum Mechanical CalculationsN-(Diphenylmethylene)acetamide (1) has been studied by X-ray crystallography as an example for the polyfunctional, highly reactive N-methyleneamides. The dihedral angle (C = N - C = O = 73°) and the bond lengths indicate that there is only little interaction between the C = O and the C = N groups. Extensive ab initio 3-21G calculations for the parent molecule H2C = N - CH = O (2) predict a C - N rotational barrier of ca. 4 kcal/mol with a cisoid form (C = N - C = O = 23°) as the most stable structure. MNDO data as well as spectroscopic properties (IR, 13C NMR) suggest high molecular flexibility due to the many electronic interactions possible for the nitrogen atom.
    Notes: Als Beispiel für die polyfunktionellen N-Methylencarbonsäureamide wurde N-(Diphenylmethylen)acetamid (1) röntgenographisch untersucht. C = N - C = O-Torsionswinkel (73°) und Bindungslängen deuten auf nur geringe Wechselwirkungen zwischen C = O- und C = N-Molekülteil. Ausführliche ab initio-3-21G-Berechnungen am Grundsystem H2C = N - CH = O (2) sagen eine C - N-Rotationsbarriere von ca. 4 kcal/mol voraus, wobei als stabilste Struktur eine cisoide Form (C = N - C = O-Winkel = 23°) gefunden wurde. MNDO-Daten und spektroskopische Untersuchungen (IR, 13C-NMR) deuten ebenfalls auf hohe molekulare Beweglichkeit, die vor allem durch die vielfältigen elektronischen Wechselwirkungsmöglichkeiten des Stickstoffatoms verursacht wird.
    Additional Material: 3 Ill.
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    URL: http://dx.doi.org/10.1002/cber.19841170428
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    Reduktion von β-Lactamen, I. Reduktion von 3,3,3′,3′-Tetramethyl[1,1′-biazetidin]-2,2′-dion mit komplexen Hydriden (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1659-1670 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reduction of β-Lactams, I. Reduction of 3,3,3′,3′-Tetramethyl[1,1′-biazetidine]-2,2′-dione with Complex HydridesReduction of the title compound 7 with lithium aluminium hydride leads to four products 8 to 11 in yields depending on the reaction conditions. Compounds 8 to 10 are also obtained from the bicyclic hydrazide 12, isomeric with 7. Therefore, the reduction of 7 and 12 is likely to proceed in part via common intermediates. A reaction scheme is proposed to account for the generation of the products. With other hydride reagents complex reaction mixtures are obtained from 7. The reduction of 7 to 3,3,3′,3′-tetramethyl-1,1′-biazetidine (13) failed.
    Notes: Die Reduktion der Titelverbindung 7 mit Lithiumaluminiumhydrid liefert die vier Produkte 8 - 11 in von den Reaktionsbedingungen abhängigen Mengenverhältnissen. Da die Verbindungen 8 - 10 auch aus dem mit 7 isomeren bicyclischen Hydrazid 12 erhalten werden, muß die Reduktion von 7 und 12 z. T. einheitlich ablaufen. Hierfür wird ein Reaktionsschema vorgeschlagen. Mit anderen Hydridübertragungsreagenizen entstehen aus 7 komplexe Produktgemische. Die Reduktion von 7 zu 3,3,3′,3′-Tetramethyl-1,1′-biazetidin (13) gelang nicht.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170503
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    Synthese von (Trimethylstannyl)adamantan-Derivaten (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 565-574 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of (Trimethylstannyl)adamantane DerivativesReaction of brominated adamantane compounds with (trimethylstannyl)lithium afforded a series of (trimethylstannyl)adamantane derivatives. Additionally, we found products from fragmentation and reduction reactions which allowed conclusions concerning the mechanisms. Surprisingly high stereoselectivities were observed in most instances. By Wurtz synthesis we obtained 2-adamantyltriphenylstannane.
    Notes: Die Umsetzung bromierter Adamantanverbindungen mit (Trimethylstannyl)lithium lieferte eine Reihe von (Trimethylstannyl)adamantan-Derivaten. Wir fanden zusätzlich Fragmentierungs- und Reduktionsprodukte, die Rückschlüsse auf den Mechanismus zuließen. Überraschend ist die hohe Stereoselektivität der meisten Reaktionen. Durch Wurtz-Synthese wurde auch 2-Adamantyltriphenylstannan erhalten.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170212
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    Substituenteneinflüsse auf das Valenzgleichgewicht 4,8-substituierter Homotropilidene (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 575-584 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Influence of Substituents on the Valence-tautomeric Equilibrium of 4,8-Substituted HomotropilidenesThe valence-tautomeric equilibrium of 4,8-substituted homotropilidenes 2 - 4 is governed by electronic (preference of a substituent for attachment to a cyclopropyl or an aliphatic carbon atom) and steric factors. The conformational change chair → boat, which precedes the Cope rearrangement of a homotropilidene, cannot take place when both endo-8- and cis-4-substituents are present.
    Notes: Das Valenzgleichgewicht 4,8-substituierter Homotropilidene 2 - 4 wird durch elektronische (Präferenz eines Substituenten für Cyclopropyl- oder aliphatische Verknüpfung) und sterische Faktoren bestimmt. Die der Cope-Umlagerung vorgeschaltete Konformationsänderung Sessel → Boot wird verhindert, wenn das Homotropiliden sowohl in endo-8- wie in cis-4-Stellung substituiert ist.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170213
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    Heterocyclische β-Enaminoester, 311). Neue 6:7-, 6:8- und 5:6:7-Kombinationen heterokondensierter Pyrimidine aus den Iminophosphoranen heterocyclischer β-Enaminoester. - Stabile heterocyclische Ylide (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 585-621 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heterocyclic β-Enamino Esters, 311). Novel 6:7-, 6:8, and 5:6:7-Combinations of Heterocondensed Pyrimidines from Iminophosphoranes of Heterocyclic β-Enamino Esters. - Stable Heterocyclic YlidesWith acetylenic esters the (5-azolylimino)triphenylphosphoranes 10a - d do not show any cyclo-addition tendency, while the (2-thienylimino)triphenylphosphoranes 8a, b yield the stable ylids 13a, b. By treatment with phenyl isocyanate the iminophosphoranes 16a - m, 17, and 18a, b afford the carbodiimides 19a - m, 20, and 21a, b; however, 10b - d give the O-ethylisoureas 24b - d. 19a, b, e, f, h are transformed in aqueous ethanol into 6:7-bicycles, namely into oxepino[2,3-d]pyrimidines 25a, b, e, f, h. With isopropylamine the 2-isopropylamino-6:7-bicycles 31a - c, e - h are formed analogously, while in the case of thiocin 21a the 6:8-bicycle 34 is obtained. The salts 33f, g are formed by treating 19f, g or 25f with aqueous diethylamine. Accordingly, 2-aminoethanol, 3-aminopropanol, and ethylenediamine react with 19a, b, f, l to afford the 2-hydroxy- and 2-aminoalkyl-6:7-bicycles 36a - f; by treatment with hydrazine the 2-hydrazinooxepino- and -thiepino[2,3-d]pyrimidines 38a - h and 39 are obtained, which are converted with functional C1-units into 5:6:7-tricycles 43a - d, 45'a, b.
    Notes: Die (5-Azolylimino)triphenylphosphorane 10a - d zeigen mit Acetylendicarbonsäureestern keine Tendenz zur Cycloaddition, während die (2-Thienylimino)triphenylphosphorane 8a, b, zu den stabilen Yliden 13a, b reagieren. Mit Phenylisocyanat ergeben die Iminophosphorane 16a - m, 17 und 18a, b die Carbodiimide 19a - m, 20 und 21a, b; 10b - d liefern statt dessen die O-Ethylisoharnstoffe 24b - d. In wäßrigem Ethanol werden 19a, b, e, f, h in 6:7-Bicyclen, nämlich in die Oxepino[2,3-d]pyrimidine 25a, b, e, f, h umgewandelt. Mit Isopropylamin bilden sich die 2-Isopropylamino-6:7-Bicyclen 31a - c, e - h und im Fall des Thiocins 21a der 6:8-Bicyclus 34. Die Salze 33f, g entstehen durch Einwirkung von wäßrigem Diethylamin auf 19f, g bzw. auf 25f. 2-Aminoethanol, 3-Aminopropanol und Ethylendiamin ergeben mit 19a, b, f. l analog die 2-Hydroxy- und 2-Aminoalkyl-6:7-Bicyclen 36a - f; mit Hydrazin werden die 2-Hydrazinooxepino- und -thiepino[2,3-d]pyrimidine 38a - h und 39 erhalten, die mit funktionellen C1-Bausteinen zu den 5:6:7-Tricyclen 43a - d, 45'a, b führen.
    Additional Material: 24 Tab.
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    URL: http://dx.doi.org/10.1002/cber.19841170214
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    Addition von Aldehyden an aktivierte Doppelbindungen, XXXIV1). Addition von Aldehyden an cyclische α-Methylenketone (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 682-693 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Addition of Aldehydes to Activated Double Bonds, XXXIV1). Addition of Aldehydes to Cyclic α-Methylene KetonesThe thiazolium salt-catalyzed addition of aldehydes to the cyclic α-methylene ketones 3, 4, 7, 8, 48, and 49 leads to γ-diketones 9 - 22, 50 - 53; some of them were converted into unsaturated ketones 23 - 28, pyrroles 29 - 34, 37 - 43, and furans 35, 36, 44 - 46. The α-methylene ketones were synthesized by retro Diels-Alder reaction of the corresponding norbornene compounds 1, 2, 5, 6, 47.
    Notes: Die Thiazoliumsalz-katalysierte Addition von Aldehyden an die cyclischen α-Methylenketone 3, 4, 7, 8, 48 und 49 führt zu γ-Diketonen 9 - 22, 50 - 53, aus denen einige ungesättigte Ketone 23 - 28, Pyrrol- 29 - 34, 37 - 43 und Furanderivate 35, 36, 44 - 46 synthetisiert wurden. Die Darstellung der α-Methylenketone erfolgte durch Retrospaltung entsprechender Norbornenderivate 1, 2, 5, 6 und 47.
    Additional Material: 7 Tab.
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    URL: http://dx.doi.org/10.1002/cber.19841170221
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    Diazadienes as Controlling Ligands in Catalysis, 51). Synthesis of Chiral Diazadienes R* - N = CR' - CR' = N - R* (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 694-701 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Diazadiene als Steuerliganden in der Katalyse, 51). Synthese chiraler Diazadiene R* - N = CR' - CR' = N - R*Die im Prinzip einfache Kondensationsreaktion von Glyoxal (als Hydrat) und 2,3-Butandion mit primären Aminen führt leider bei aliphatischen Aminen mit tertiärem bzw. sekundärem α-Kohlenstoff oftmals zu unerwünschten Additionsprodukten. Unter speziellen Synthesebedingungen können mit (R)-1-Phenylethylamin (1) und (1S,2S,3S,5R)-3-(Aminomethyl)pinan die gewünschten Diimine (Diazadiene (dad): R* - N = CR' - CR' = N - R*, R' = H, CH3) 4, 6 - 8 erhalten werden. Aus (S)-2-Amino-1-butanol (3) werden je nach Dion-Komponente ein Morpholinomorpholin 9 bzw. ein Bioxazolidin 10 gebildet, die von elektronenreichen Metallen in ihrer isomeren Form als Diazadiene gebunden werden ((dad)Mo(CO)4 11 und 12). Die offenkettige dad-Form ist durch O-Silylierung (14, 15) stabilisierbar. Die (dad)Eisen(0)-katalysierte Dimerisierung von Butadien zu 4-Vinyl-1-cyclohexen mit diesen dad-Liganden ergibt Enantiomerenüberschüsse e.e. bis zu 16%.
    Notes: The condensation of glyoxal (as hydrate) or 2,3-butanedione with primary amines is, in principle, a simple reaction. Unfortunately, aliphatic amines with secondary or tertiary α-carbons often give unwanted addition products. Under special reaction conditions the desired diimines (diazadienes (dad): R* - N = CR' - CR' = N - R*, R' = H, CH3) 4, and 6 - 8 are obtained from (R-1-phenyl-ethylamine (1) and (1S,2S,3S,5R)-3-(aminomethyl)pinane (2). Depending on the dione, a morpholinomorpholine 9 and a bioxazolidine 10 are formed from (S)-2-amino-1-butanol (3), which are bound by electron-rich metals in their isomeric dad form ((dad)Mo(CO)4 11 and 12). The acyclic dad structure is stabilized by O-silylation (14, 15). The (dad)iron(0) catalyzed dimerization of butadiene with these controlling ligands to 4-vinyl-1-cyclohexene occurs with an enantiomeric excess up to 16%.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170222
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    Anwendung der hochaufgelösten Festkörper-NMR-Spektroskopie zur Bestimmung der Ring-Ketten-Tautomerie (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 702-709 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Application of High-Resolution Solid State NMR Spectroscopy for the Determination of the Ring-Chain TautomerismThe structure of the benzaldehyde derivatives 1 and 2 showing ring-chain tautomerism was investigated by NMR spectroscopy in the solid state and in solution. Difficulties in preparing single crystals, low solubility, and the presence of solvent in the crystal prevent an X-ray analysis and other spectroscopic methods. The structural problem was solved by C-13 CP-MAS NMR spectroscopy. 2-[2-(Methylamino)ethyl]-3-nitrobenzaldoxime (1) exists in the chain form in the crystal but is in equilibrium with the cyclic isomer in solution. Two different types of crystals were obtained from the aminoethenylbenzaldehyde derivative 2, one of them containing the chain the other the cyclic form of 2. Signal assignments in the solid state result from comparison with the spectra in solution, which have been partially assigned by 2D 1H 13C NMR shift correlation.
    Notes: Die Struktur der Benzaldehyd-Derivate 1 und 2, die Ring-Ketten-Tautomerie zeigen, wird durch NMR-Spektroskopie im festen und gelösten Zustand untersucht. Schwierigkeiten beim Züchten von Einkristallen sowie die Schwerlöslichkeit bzw. die Anwesenheit von Kristallösungsmittel verhinderten die Anwendung der Röntgenstrukturanalyse und anderer spektroskopischer Methoden. Mit Hilfe von C-13-CP-MAS-NMR-Spektren wird das Strukturproblem lösbar. In 2-[2-(Methyl-amino)ethyl]-3-nitrobenzaldoxim (1) liegt im Kristall die offene Form vor, die in Lösung mit dem cyclischen Tautomeren 1b im Gleichgewicht steht. Vom Aminoethenylbenzaldehyd-Derivat 2 lassen sich zwei verschiedene Kristalle gewinnen, in denen alternativ die offene und die cyclische Struktur vorliegt. Zur Signalzuordnung werden die Festkörper-NMR-Spektren mit den z. T. durch 2D-1H-13C-NMR-Verschiebungskorrelation zugeordneten C-13-Spektren verglichen.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170223
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    Asymmetrische Katalysen, 121). Neue optisch aktive P, N-Liganden und ihr Einsatz in der Rh-katalysierten asymmetrischen Hydrierung und Hydrosilylierung (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 710-724 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Asymmetric Catalyses, 121). New Optically Active P,N Ligands and Their Use in Rh-Catalyzed Asymmetric Hydrogenation and HydrosilylationNew P,N-ligands 2, 4 and 5 were prepared by Schiff base condensation of (2-formylphenyl)diphenyl- and tris(2-formylphenyl)phosphane with (R)-(+)-1-phenylethylamine and ethylenediamine. (R)-(+)-aminphos (6) was obtained by hydrogenation of the C = N bond in (R)-(+)-iminphos (2). The new imine ligands form stable chelate complexes. The pseudotetrahedral CpFe(CO)[R)-(+)-iminphos]PF6 was separated into the diastereoisomes with respect to the Fe configuration. The square planar Rh[(R)-(+)-iminphos]2X is obtained as a cis/trans mixture. The isolated Rh complexes and the combinations [Rh(COD)Cl]2/2, 4, and 6, respectively, were used as catalysts for the homogeneous hydrogenation of (Z)-α-(acetylamino)cinnamic acid and for the hydrosilylation of acetophenone with diphenysilane. The optical yield of 1-phenyl-ethanol, the product of hydrolysis of the hydrosilylation, increases with increasing ligand excess, decreasing catalyst concentration, and decreasing temperature.
    Notes: Neue P,N-Liganden 2, 4 und 5 wurden durch Schiffbasenkondensation von (2-Formylphenyl)diphenyl- und Tris(2-formylphenyl)phosphan mit (R)-(+)-1-Phenylethylamin und Ethylendiamin dargestellt. (R)-(+)-aminphos (6) wurde durch Hydrierung der C = N-Bindung in (R)-(+)-iminphos (2) erhalten. Die neuen Imin-Liganden bilden stabile Chelatkomplexe. Das pseudotetraedrische CpFe(CO)[(R)-(+)-iminphos]PF6 wurde in die Diastereomeren bezüglich der Fe-Konfiguration getrennt. Das quadratisch-planare Rh[(R)-(+)-iminphos]2X fällt als cis/trans-Gemisch an. Die isolierten Rh-Komplexe und die Kombinationen [Rh(COD)Cl]2/ 2, 4 bzw. 6 wurden als Katalysatoren für die homogene Hydrierung von (Z)-α-(Acetylamino)zimtsäure und für die Hydrosilylierung von Acetophenon mit Diphenylsilan eingesetzt. Die optische Ausbeute an 1-Phenylethanol, dem Hydrolyseprodukt der Hydrosilylierung, steigt mit zunehmendem Ligandenüberschuß, mit abnehmender Katalysatorkonzentration und mit abnehmender Temperatur.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170224
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    Synthese und Solvolyse von (Z)/(E)-1-Methyl-2-[2-(1-propin-1-yl)phenyl]vinyl-triflat und 1-Methylen-2-[2-(1-propin-1-yl)-phenyl]ethyl-triflat (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 3021-3033 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis and Solvolysis of (Z)/(E)-1-Methyl-2-[2-(1-propyn-1-yl)phenyl]vinyl Triflate and 1-Methylene-2-[2-(1-propyn-1-yl)phenyl]ethyl TriflateThe synthesis and solvolysis of the triflates (Z)/(E)-8 and 20 in various solvents are described. The (E)-triflate 8 reacts in trifluoroethanol by rearrangement via the intermediate naphthyl cation 9 to give the naphthyl ether 22 and the naphthyl triflate 24. The identification of 1-bromo-2,3-dimethylnaphthalene (26) after addition of bromide ions to the solvolysis confirms 9 as a reactive intermediate. The (Z)-triflate 8 solvolyses preferably to the elimination product 28, the formation of [(3-methyl-2-naphthyl)methyl] (trifluoroethyl) ether (23), however, can not be explained via the cation 9 as an intermediate. The solvolysis of the triflate 20 leads also to the rearranged products 22 and 23.
    Notes: Die Synthese und Solvolyse der Triflate (Z)/(E)-8 und 20 in verschiedenen Lösungsmitteln wird beschrieben. Das (E)-Triflat 8 reagiert in Trifluorethanol bevorzugt unter Umlagerung über das intermediäre Naphthylkation 9 zum Naphthylether 22 und zum Naphthyltriflat 24. Der Nachweis von 1-Brom-2,3-dimethylnaphthalin (26) nach Bromidionenzusatz zur Solvolyse bestätigt 9 als reaktive Zwischenstufe. Das (Z)-Triflat 8 solvolysiert bevorzugt zum Eliminierungsprodukt 28, die Bildung des [(3-Methyl-2-naphthyl)methyl]-(trifluorethyl)-ethers (23) kann jedoch nicht über das Kation 9 als Zwischenstufe erklärt werden. Die Solvolyse des Triflates 20 führt ebenfalls zu den Umlagerungsprodukten 22 und 23.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841171004
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  • 78
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    Notizen.Bestimmung absoluter Geschwindigkeitskonstanten bei der radikalischen Addition an Alkene nach der “Quecksilbermethode” (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 3160-3164 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Measurement of Absolute Rates of Radical Additions to Alkenes by the “Mercury Method”Using the 5-hexenyl radical (2) as “radical clock” the rates of radical additions to methyl acrylate (5a) and acrylonitrile (5b) are measured by the “mercury method” (Table 1). Alkyl radicals are trapped by the alkylmercury hydride 1 with rate constants of at least 107 1 · mol-1 · s-1.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841171015
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  • 79
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    Masthead (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984) 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841171101
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  • 80
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    Radikalkettenreaktionen mit Maleinsäureanhydriden  -  Zur kontrathermodynamischen Stereoselektivität (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 3175-3182 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Radical Chain Reactions with Maleic Anhydrides  -  Contrathermodynamic StereoselectivityThe reactions of cyclohexylmercuric chloride with NaBH4 and alkenes 1a-g yield 60-84% of products 3, 4 and 6 in a radical chain process (table 1). Caused by steric effects of substituents Z at least 97% of the radical attack occurs at the unsubstituted carbon atom of maleic anhydrides 1c-g. Only fluoromaleic anhydride 1b is attacked by cyclohexyl radicals predominantly at the substituted carbon atom, because fluorine is a tiny, electron releasing substituent. Radicals 2 are trapped predominantly from the anti-direction by the H-donor (figure 1), yielding cis-compounds 3 as main products. This „contrathermodynamic“ stereoselectivity ranges between 2.3 and 19 (table 1).
    Notes: Die Reaktion von Cyclohexylquecksilberchlorid mit NaBH4 und den Alkenen 1a-g liefert in einer Radikalkettenreaktion die Produkte 3, 4 und 6 in 60- bis 84proz. Ausbeuten (s. Tab. 1). Wegen der sterischen Effekte der Substituenten Z erfolgt der Angriff der Radikale zu mindestens 97% am unsubstituierten C-Atom der Maleinsäureanhydride 1c-g. Allein das Fluormaleinsäureanhydrid 1b wird bevorzugt am substituierten C-Atom durch Cyclohexyl-Radikale angegriffen. Die Ursache für diese umgekehrte Regioselektivität liegt in der geringen Raumerfüllung und dem elektronenspendenden Effekt des Fluoratoms. Die H-Übertragung auf die Radikale 2 erfolgt überwiegend von der anti-Seite (s. Abb. 1), so daß die thermodynamisch instabileren cis-Verbindungen 3 als Hauptprodukte entstehen. Diese „kontrathermodynamische“ Stereoselektivität liegt zwischen 2.3 und 19 (s. Tab. 1).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841171103
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  • 81
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    Reaktive Platin-Komplexe mit α-Aminosäurederivaten und ihre P- und N-Kernresonanzspektren (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1241-1245 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactive Platinum Complexes with α-Amino Acid Derivatives and their 31P- and 15N Nuclear Magnetic Resonance SpectraThe α-amino acidate chelate complexes (n-Bu3P)(Cl)⊓PtNH2CH(R)COO (1a - c) (R = H, CH3, CHMe2) react with thionyl chloride, phosphorus pentachloride, or acetyl chloride by cleavage of the chelate ring to give complexes with α-amino acyl chloride or acetic glycine anhydride as ligands: (n-Bu3P)Cl2Pt(NH2CH2COCl) (2), (n-Bu3P)Cl4Pt(NH2CH(CHMe2)COCl) (6), (n-Bu3P)-Cl2Pt(NH2CH2CO(O)OCCH3) (4). Using 15N enriched amino acids, the IR, 15N and 31P NMR spectra indicate cis orientation of phosphane and amino groups in all these complexes.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170336
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  • 82
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    Synthesen mit Alkendiazoniumsalzen, III. ω,ω′-Di-1H-1,2,3-triazolylalkane aus Ethendiazonium- hexachloroantimonaten und ω,ω′-Diaminoalkanen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1246-1249 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Syntheses with Alkenediazonium Salts, III. ω,ω′-Di-1H-1,2,3-triazolylalkanes from Ethenediazonium Hexachloroantimonates and ω,ω′-DiaminoalkanesReaction of the ethenediazonium hexachloroantimonates 2 with ω,ω′-diaminoalkanes 3 leads to ω,ω′-di-1H-1,2,3-triazolylalkanes 5.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170337
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  • 83
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    Beiträge zur Chemie des Bors, 135. Additionsverbindungen von 1,3,2-Diazaborolidinen mit Aluminium- und Galliumhalogeniden (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1222-1234 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Contributions to the Chemistry of Boron, 1351). Addition Compounds of 1,3,2-Diazaborolidines with Aluminium and Gallium Halides1,3-Dimethyl-1,3,2-diazaborolidines 3 - 6 add aluminium and gallium halides, respectively, in a 1 : 1 molar ratio. The ligand is monodentate in these coordination compounds (3a - e, 4a, 5a, b, 6a). Addition occurs at one of the ring nitrogen atoms irrespective of the B-substituent. A consequence of this coordination is a long BN bond to the chiral tetracoordinated nitrogen atom as well as a considerable shortening of the BN bond involving the tricoordinate ring nitrogen. In addition, the almost planar five-membered ring adopts the envelope conformation as shown by an X-ray structure analysis of 5a. In contrast, the 2-(dimethylamino)diazaborolidine 7 yields unstable 1 : 1 besides stable 1 : 2 adducts 8. In these the Lewis acid is also coordinated to the ring nitrogen atoms only.
    Notes: Die 1,3-Dimethyl-1,3,2-diazaborolidine 3 - 6 addieren Aluminium- oder Galliumhalogenide im Molverhältnis 1 : 1 zu Koordinationsverbindungen 3a - e, 4a, 5a, b, 6a, in denen der Ligand einzähnig ist. Die Anlagerung erfolgt unabhängig vom B-Substituenten an einem Ringstickstoff-Atom. Folge dieser Koordination ist die Ausbildung einer langen BN-Bindung zum chiralen tetra-koordinierten Ring-Stickstoff, eine erhebliche Verkürzung der BN-Bindung zum dreifach koordinierten endocyclischen Stickstoffatom und der Übergang des nahezu planaren Fünfrings in die „envelope“-Konformation, wie die Röntgenstrukturanalyse von 5a belegt. Im Gegensatz dazu liefert das 2-(Dimethylamino)diazaborolidin 7 mit AlX3 und GaX3 instabile 1 : 1- und stabile 1 : 2-Addukte 8. In diesen ist die Lewis-Säure nur an den Ringstickstoff-Atomen koordiniert.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170334
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  • 84
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    Eine einfache Synthese primärer Amine über ihre N,N-Bis(trimethylsilyl)-Derivate (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1250-1254 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A Simple Synthesis of Primary Amines via their N,N-Bis(trimethylsilyl) DerivativesPrimary halogen compounds 1 or the corresponding tosylates react with sodium bis(trimethylsilyl)amide (2) in hexamethyldisilazine to form N,N-bis(trimethylsilyl)amines 3, which are converted into the amine hydrochlorides 5 by treatment with aqueous HCl.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170338
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  • 85
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    Dibenz[a,j]anthracene via Photo-cyclodehydrogenation of 9,10-Dihydro-2-styrylphenanthrene (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1255-1258 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Dibenz[a,j]anthracen durch Photocyclodehydrierung von 9,10-Dihydro-2-styrylphenanthrenWährend aus 2-Styrylphenanthren (1) durch Photocyclodehydrierung Benzo[c]chrysen (2) entsteht, läßt sich unter Ausnutzung der „ΣF*-Regel“5) aus 9,10-Dihydro-2-styrylphenanthren (4) durch Photocyclodehydrierung zu 6 und anschließende Dehydrierung Dibenz[a,j]anthracen (3) erhalten.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170339
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  • 86
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    Eine einfache Synthese der 5-Cyan-2-pyridincarbonsäure und ihres Amids (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1259-1261 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A Simple Synthesis of 5-Cyano-2-pyridinecarboxylic Acid and its AmideThe title compounds 3 and 2 (X = CN) are prepared in good yields by regioselective carbamoylation of 3-cyanopyridine in a Minisci reaction and by consecutive amide hydrolysis with amyl nitrite in HCl-saturated acetic acid. The observed regioselectivity apparently remains confined to carbamoyl and possibly acyl radicals and to - M-effect substituents in 3-position.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170340
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  • 87
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    Masthead (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984) 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170401
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  • 88
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    Masthead (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984) 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170101
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  • 89
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    Zur Umsetzung von 2-Pyrrolcarbaldehyd mit heterosubstituierten Ethenen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1424-1435 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: On the Reaction of 2-Pyrrolecarbaldehyde with Hetero-substituted Ethenes3H-Pyrrolizines 1 have been obtained from reactions of 2-pyrrolecarbaldehyde with ethenylphosphonates 2 and the phosphane oxide 5, respectively, the ratio of products depending on the structure of the educts. On varying the reaction conditions a controlled synthesis of both isomers 1e/f was achieved. Pyrrolizines, formed in a reaction of 2 pyrrolecarbaldehyde with ethenyl phenyl sulfone (3), could not be isolated since the reaction proceeded to give more complex pyrrolizine derivatives and the cyclazine 11. A mechanism is proposed for this multistep reaction. N-Alkylation of 2-pyrrolecarbaldehyde with dihaloalkanes has been carried out using phase transfer catalysis.
    Notes: Umsetzungen des 2-Pyrrolcarbaldehyds mit Ethenylphosphonaten 2 und dem Phosphanoxid 5 führten zu 3H-Pyrrolizinen 1, wobei das Mengenverhältnis der gebildeten Isomeren von der Struktur der Edukte abhängt. In einem Falle (1e/1f) gelang die gezielte Synthese beider Isomeren durch Variation der Reaktionsbedingungen. Die aus 2-Pyrrolcarbaldehyd und Ethenylphenylsulfon (3) entstandenen Pyrrolizine 1e/f reagieren weiter unter Bildung komplexer Pyrrolizinderivate und des Cyclazins 11. Für diese Mehrstufenreaktion wird ein Mechanismus vorgeschlagen. Unter Phasentransfer-Bedingungen gelingen Alkylierungen des 2-Pyrrolcarbaldehyds mit Dihalogenalkanen.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170413
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  • 90
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    Anodische Oxidation von Organoborverbindungen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 1400-1423 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Anodic Oxidation of OrganoboranesOrganoboranes are converted into more easily oxidizable borates by reaction with nucleophiles and the alkyl groups are dimerized by anodic oxidation. The oxidation potentials (Ep) of the borates depend strongly on the nature of the complexing nucleophile, for instance Ep = +0.37V (vs. SCE) with OH- or +1.65V with tetrahydrofuran. The dimer yields are optimized with trioctylborane (5) by variation of the electrode material and the electrolyte. At the platinum anode in sodium hydroxide-methanol/tetrahydrofuran yields of 80% are obtained for acyclic alkyl groups, and lower ones for cycloalkyl groups. They exceed those obtained by the Kolbe electrolysis or the oxidation with neutral hydrogen peroxide and they are comparable to those of the AgNO3 oxidation. - The selective preparation of unsymmetrical products from borates with different alkyl groups is not possible, the dimerization proceeds likely via free radicals that couple statistically. Good yields of unsymmetrical coupling products are achieved, when one olefin is used in excess. With chloro-, ethoxy-, acetoxy-, and aryl-substituted alkyl groups the dimers are obtained in 21 - 66% yield, with bromide the yield are lower and with nitriles the dimerization fails.
    Notes: Organoborane werden durch Nucleophile in leichter oxidierbare Borate übergeführt und die Alkylreste durch anodische Oxidation dimerisiert. Die Oxidationspotentiale (Ep) der Borate werden stark vom komplexierenden Nucleophil beeinflußt, z. B. Ep = +0.37V (gKE) mit OH- oder + 1.65 V mit Tetrahydrofuran. Mit Trioctylboran (5) werden die Dimerenausbeuten (10) durch Variation von Elektrodenmaterial und Elektrolyt optimiert. An der Platinanode in KOH-Methanol/Tetrahydrofuran liegen die Ausbeuten für acyclische Alkylreste um 80%, die für Cycloalkane niedriger. Sie übertreffen die der Kolbe-Elektrolyse oder der Oxidation mit neutralem Wasserstoffperoxid und sind denen bei der Oxidation mit Silbernitrat vergleichbar. - Die selektive Darstellung unsymmetrischer Produkte aus Boraten mit unterschiedlichen Alkylresten gelingt nicht; die Dimerisierung verläuft wahrscheinlich über freie Radikale, die statistisch kuppeln. Gute Ausbeuten an unsymmetrischen Kupplungsprodukten werden jedoch erzielt, wenn ein Olefin im Überschuß eingesetzt wird. Mit chlor-, ether-, ester- und arylsubstituierten Alkylresten erhält man Dimere mit 21 - 66% Ausbeute. Mit Bromiden gelingt die Kupplung schlecht, mit Nitrilen überhaupt nicht.
    Additional Material: 12 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170412
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    Hetero-π-Systeme, 9. Über die Beziehungen zwischen Silaethenen und Methylsilylenen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 2369-2381 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Hetero-π-Systems, 9. About the Relationships between Silaethenes and MethylsilylenesSilaethenes 1 and the isomeric methylsilylenes 2 are separately existing species, but can readily be interconverted in an argon matrix via a photochemically induced 1,2-H shift. In case of the thermal excitation in the gas phase examples for both directions have been detected spectroscopically: the isomerisation of a silaolefin into the corresponding silylene (1d → 2d) and the formation of a silene from a silylene (2f → 1f).
    Notes: Die Silaolefine 1 und dazu isomeren Methylsilylene 2 sind getrennt existenzfähige Spezies, lassen sich in einer Argonmatrix aber über eine photochemisch induzierte 1,2-H-Wanderung leicht ineinander umwandeln. Bei thermischer Anregung in der Gasphase ist sowohl die Isomerisierung eines Silaolefins zum zugehörigen Silylen (1d → 2d) als auch eines Silylens zum entsprechenden Silen (2f → 1f) direkt spektroskopisch nachweisbar.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170709
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  • 92
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    Cyclopropene als Komplexliganden: η4-Vinylketen-Komplexe des Mangans, Vanadiums und Cobalts; präparative und röntgenographische Ergebnisse (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 2469-2478 
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    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Cyclopropenes as Complex Ligands: η4-Vinylketene Complexes of Manganese, Vanadium, and Cobalt; Preparative and X-ray Crystallographic ResultsThe reaction of 1,2,3-triphenylcyclopropene with (η5-C5H5)Mn(CO)3, (η5-C5H5)V(CO)4, (η5-C5H5)Co(CO)2 and Co2(CO)8 yields via ring opening and carbonylation the new compounds LMn(C5H5)CO (1), LV(C5H5)(CO)2 (2), LCo(C5H5) (3, 4) and L2Co2(CO)4 (6) (L = η4-C3Ph3HCO), respectively. In the reaction with (η5-C5H5)Co(CO)2 additionally the formation of 2,3-diphenylindenone (5) is observed. The X-ray structures of 1, 3 and 5 have been determined.
    Notes: Die Umsetzung von 1,2,3-Triphenylcyclopropen mit (η5-C5H5)Mn(CO)3, (η5-C5H5)V(CO)4, (η5-C5H5)Co(CO)2 und Co2(CO)8 ergibt unter Ringöffnung und Carbonylierung die neuen Verbindungen LMn(C5H5)CO (1), LV(C5H5)(CO)2 (2), LCo(C5H5) (3, 4) bzw. L2CO2(CO)4 (6) (L = η4-C3Ph3HCO). Bei der Reaktion mit (η5-C5H5)Co(CO)2 wird außerdem die Bildung von 2,3-Diphenylindenon (5) beobachtet. Die Röntgenstrukturen von 1, 3 und 5 wurden bestimmt.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170718
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    Desaminierungsreaktionen, 40. Zerfall von 3,3-, 5,5- und 7,7-Dimethyl-2-norbornan-diazonium-Ionen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 2510-2523 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Deamination Reactions, 401). Decomposition of 3,3-, 5,5-, and 7,7-Dimethyl-2-norbornanediazonium Ionsgem.-Dimethylnorbornyl cations (3, 5) were generated by decomposition of optically active diazonium ion precursors. 6,1- and 6,2-H shifts were detected by structural isomerization and racemization, respectively. Product distributions and optical activities were profoundly affected by the polarity of the solvent. In weakly polar solvents, substitution reactions were associated with much less racemization than hydrogen shifts. Our observations are incompatible with equilibrating open ions but are reasonably explained in terms of unsymmetrical ion pairs.
    Notes: gem.-Dimethylnorbornylkationen (3,5) wurden durch Zerfall optisch aktiver Diazonium-Ionen erzeugt. 6,1- und 6,2-H-Verschiebungen wurden durch Strukturisomerisierung bzw. Racemisierung nachgewiesen. Die Polarität des Lösungsmittels hatte einen starken Einfluß auf Verteilung und optische Aktivität der Produkte. In schwach polaren Lösungsmitteln war die Substitution mit deutlich weniger Racemisierung verbunden als die H-Verschiebung. Unsere Beobachtungen sind mit äquilibrierenden, offenen Carbokationen unvereinbar, werden aber durch unsymmetrische Ionenpaare plausibel gedeutet.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170722
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  • 94
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    Notizen. Addition von Carbonsäuren an (1S)-5,5-Dimethylbicyclo[2.2.1]hept-2-en (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 2524-2526 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Addition of Carboxylic Acids to (1S)-5,5-Dimethylbicyclo[2.2.1]hept-2-eneProtonation of the title compound 5 induced Wagner-Meerwein rearrangement and 6,2(6,1)-hydride shifts, depending on the polarity of the acid (trifluoroacetic, acetic, and 2-ethylhexanoic acid). The optical purity of 5,5-dimethyl-2-norbornyl esters (7) exceeded that of 7,7-dimethyl-2-norbornyl esters (9). The results are interpreted in terms of asymmetric ion pairs which are tighter than those involved in deamination reactions.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170723
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  • 95
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    Cäsium-Effekt bei C-C-Bindungsknüpfungen zu vielgliedrigen Kohlenwasserstoff-Ringen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 2538-2541 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cesium Effect in C-C-Bond Forming Reactions Yielding Large Hydrocarbon RingsC-C-bond formations of the Wurtz type following the Müller-Röscheisen procedure [alkali metal + tetraphenylethene (TPE)] leading to [2n]paracyclophane rings 2 have been carried out, comparing sodium, potassium, and cesium as metals. As fig. 1 shows, the selectivity of the oligomer formation starting from 1,4-bis(chloromethyl)benzene (1a) is strongly dependent on the alkali metal used. Sodium/TPE besides 2b predominantly yields the higher oligomers 2c - e. Use of cesium metal/TPE leads to 2b preferentially. With potassium metal/TPE all oligomers 2b - e are obtained in low yields or traces, respectively. According to these results, the oligomer formation in carbocyclic ring systems can be steered by the type of alkali metal applied; cesium seems to favour the formation of conformationally more rigid rings (like 2b).
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170726
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  • 96
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    Intramolekulare [4 + 3]-Cycloaddition von Allylium-2-olaten (Oxallylen) an den Furan-Kern: Synthese Sauerstoff-überbrückter Octahydroazulene und -benzocycloheptene (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 2580-2596 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Intramolecular [4 + 3] Cycloaddition of Allylium-2-olates (Oxallyls) to the Furan Nucleus: Synthesis of Oxy-bridged Octahydro-azulenes and -benzocycloheptenesThe grignard reagents prepared from the 2-(ω-chloroalkyl)furans 3b, c can be acylated with the anhydrides or chlorides of chloroacetic, dichloroacetic, and α-chloropropionic acid to form the ω-furyl-substituted α-chloro ketones 1a - d. Treatment of 1 with the lithium perchlorate/triethylamine reagent affords the octahydroepoxyazulenones 2a - c and -1H-benzocycloheptenone 2d, respectively. In the case of 2b and c the exo-connection at C-8a, i.e. trans-anellation of the carbocyclic rings, is preferred.
    Notes: Die aus den 2-(ω-Chloralkyl)furanen 3b, c hergestellten Grignard-Verbindungen können mit den Anhydriden oder Chloriden von Chloressigsäure, Dichloressigsäure und α-Chlorpropionsäure acyliert werden. Die so gebildeten ω-furylsubstituierten α-Chlorketone 1a - d liefern bei der Behandlung mit dem Lithiumperchlorat/Triethylamin-Reagens die Octahydroepoxyazulenone 2a - c und das Octahydroepoxy-1H-benzocycloheptenon 2d. Im Falle von 2b und c ist die exo-Verknüpfung an C-8a, d. h. die trans-Anellierung der carbocyclischen Ringe, bevorzugt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170804
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  • 97
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    Naphtho[b]cycloheptatrienyliden - ein Carben der Tropyliden-Reihe mit neuartigen Eigenschaften (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 2644-2659 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Naphtho[b]cycloheptatrienylidene - a Carbene of the Tropylidene Series with Novel PropertiesNaphtho[b]tropylidene (3) possesses a [15]annulene skeleton. It can be generated by flash solvolysis of the sodium salt of naphthotropone tosylhydrazone (4′) in the gas-phase. Thus 1- and 2-methylanthracene (11 and 12) are formed. The decisive step is a carbene carbene rearrangement to anthrylcarbene 6 and 10, respectively. The reaction is position-selective. Intermediates in these reactions should be the bicyclic compounds 5 and 7. In the condensed phase 3 reacts with olefins to afford cycloaddition products 16 and insertion products 17. The cycloaddition via the intermediate anthrylcarbene 6 to 18 is only a side-reaction. The bicycle system 5 formed in the carbene carbene rearrangement could be trapped by dienes to give 21. Non-stereospecific cycloaddition, allyl insertion as well as competition experiments with olefin/diene mixtures suggest an equilibrium mixture of singlet-3⇄ triplet-3⇄ bicycle 5.
    Notes: Naptho[b]tropyliden (3) besitzt ein [15]Annulen-Gerüst. Es kann durch Blitzthermolyse des Natriumsalzes des Naphthotropon-tosylhydrazons 4′ in der Gasphase erzeugt werden. Hierbei werden 1- und 2-Methylanthracen (11 und 12) gebildet. Als entscheidender Schritt läft dabei eine Carben-Carben-Umlagerung zum Anthrylcarben 6 bzw. 10 ab. Die Reaktion selbst ist positionsselektiv. Als Zwischenstufen dürften die Bicyclen 5 und 7 auftreten. In kondensierter Phase reagiert 3 mit Olefinen unter Bildung von Cycloadditionsprodukten 16 und Insertionsprodukten 17. Die Cycloaddition über das intermediäre Anthrylcarben 6 zu 18 verläuft lediglich als Nebenreaktion. Der in einer Carben-Carben-Umlagerung gebildete Bicyclus 5 konnte durch Diene zu 21 abgefangen werden. Nicht-stereospezifische Cycloaddition, Allylinsertion sowie Konkurrenzexperimente mit Olefin/Dien-Gemischen legen für 3 ein Gleichgewichtsgemisch Singulett-3 ⇄ Triplett-3 ⇄ Bicyclus 5 nahe.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170808
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    Erzeugung und Reaktivität von 1-Phosphoryl-1-(phosphoryloxy)-allyl-Anionen und verwandten Verbindungen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 2622-2643 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Formation and Reactivity of 1-Phosphoryl-1-(phosphoryloxy)allyl Anions and Related CompoundsThe formation of 1-heterosubstituted 1-phosphorylallyl anions of type 1A from the corresponding vinyl or allyl phosphonates is described. The reactivity in reactions with alkyl halides and carbonyl compounds is investigated. For preparative purposes neither the sulfur derivative 11A nor the oxygen derivatives 16A, 19A, 23A, and 29A show sufficiently high reactivity and selectivity. Only the 3-silylated derivative 25A reacts regioselectively with carbonyl compounds via Wittig-Horner olefination to give functionalized dienes 26 in moderate yields. From those it is possible to remove the phosphoryl, silyl or phosphoryloxy group selectively. Reactivity of dienes 26 in Diels-Alder reactions is poor.
    Notes: Die Bildung von in 1-Stellung heterosubstituierten 1-Phosphoryl-allyl-Anionen vom Typ 1A aus den entsprechenden Vinyl- oder Allylphosphonaten wird beschrieben und ihre Reaktivität gegenüber Alkylhalogeniden und Carbonylverbindungen untersucht. Weder das Schwefel-Derivat 11A noch die Sauerstoff-Derivate 16A, 19A, 23A und 29A besitzen für präparative Nutzung hinreichend hohe Reaktivität und Selektivität. Nur das in 3-Stellung silylierte Derivat 25A reagiert mit Carbonylverbindungen regioselektiv unter Wittig-Horner-Olefinierung in befriedigenden Ausbeuten zu den funktionalisierten Dienen 26. Aus diesen läßt sich selektiv die Phosphoryl-, die Silyl- oder Phosphoryloxygruppe abspalten. Die Reaktivität der Diene 26 in Diels-Alder-Reaktionen ist gering.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170807
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    Niederkoordinierte Phosphor-Verbindungen, 27. Synthese und Reaktionen von Ethinylphosphaalkenen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 2693-2702 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Low Coordinated Phosphorus Compounds, 27. Synthesis and Reactions of EthynylphosphaalkenesReactions of the alkyne grignards 2a, b with P-chlorophosphaalkenes 1a, b yield the ethynylphosphaalkenes 5a - d in high yields. 5a, b, d undergo [2 + 2]-cycloaddition forming the 1,3-diphosphetanes 7a, b, d. The structures of 7 are confirmed by NMR spectroscopy and, in part, by X-ray structure determination. With 2,3-dimethyl-1,3-butadiene 5a - d form the 1,2,3,6-tetra-hydrophosphinines 8a - d via [2 + 4]-cycloaddition.
    Notes: Die Umsetzung der P-Chlorphosphaalkene 1a, b mit den Grignard-Alkinen 2a, b liefert die Ethinylphosphaalkene 5a - d in hoher Ausbeute. Durch [2 + 2]-Cycloaddition entstehen daraus 1,3-Diphosphetane 7a, b, d, deren Struktur mittels NMR-Spektroskopie und Röntgenbeugung ermittelt wurde. Mit 2,3-Dimethyl-1,3-butadien erfolgt [2 + 4]-Cycloaddition zu den 1,2,3,6-Tetrahydrophosphininen 8.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170813
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    Synthese und Struktur von 2,6-Dicyanbicyclo[3.3.1]nona-2,6-dienen und 2,6-Dicyanbarbaralanen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 2745-2760 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis and Structure of 2,6-Dicyanobicyclo[3.3.1]nona-2,6-dienes and 2,6-DicyanobarbaralanesThe zinc iodide-catalyzed addition of trimethylsilyl cyanide to bicyclo[3.3.1]nonane-2,6-dione (5) yields the sterically defined O-silylated cyanohydrin 9. Trichlorophosphane oxide in pyridine converts the latter to the unsaturated dinitrile 7c. Depending on the amount of N-bromosuccinimide used, the bromination of the dinitrile 7c affords either a mixture of the monobromo- (10) and the dibromodinitrile 7d or pure dibromodinitrile 7d. With sodium methoxide in methanol the monobromodinitrile 10 is converted via concerted dehydrobromination to 2,6-dicyanobarbaralane (8c) The latter is formed almost quantitatively on debromination of the dibromodinitrile 7d with zinc/copper reagent, while sodium methoxide yields the 4-bromo-2,6-dicyanobarbaralane (12). All reactions proceed smoothly in high yields. X-ray structural parameters for bicyclo[3.3.1]nona-2,6-dienes (i. e. 7c, d and 10) and a barbaralane (i. e. 12) have for the first time become available.
    Notes: Zinkiodid-katalysierte Addition von Trimethylsilylcyanid an Bicyclo[3.3.1]nonan-2,6-dion (5) ergibt das sterisch einheitliche O-silylierte Cyanhydrin 9, das mit Trichlorphosphanoxid in Pyridin zum ungesättigten Dinitril 7c umgesetzt wird. Je nach N-Bromsuccinimid-Menge entsteht bei der Bromierung des Dinitrils 7c ein Gemisch aus Monobrom- (10) und Dibromdinitril 7d oder reines Dibromdinitril 7d. Das Monobromdinitril 10 wird durch eine konzertierte Dehydrobromierung mit Natriummethanolat in Methanol in das 2,6-Dicyanbarbaralan (8c) übergeführt. Dieses bildet sich fast quantitativ durch Debromierung des Dibromdinitrils 7d mit Zink/Kupfer, während die Dehydrobromierung von 7d mit Natriummethanolat in Methanol 4-Brom-2,6-dicyanbarbaralan (12) ergibt. Alle Reaktionen verlaufen sehr glatt und mit hohen Ausbeuten. Durch Röntgenstrukturbestimmung der Dinitrile 7c, d und 10 sowie des 4-Brom-2,6-dicyanbarbaralans (12) wurden die exo-Konfiguration der Bromatome von 7d und 10 und erstmal geometrische Parameter von Bicyclo[3.3.1]nona-2,6-dienen und einem Barbaralan ermittelt.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170817
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