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  • 1
    Electronic Resource
    Electronic Resource
    Untersuchungen an Diazoverbindungen und Aziden, XLII. (Diazomethyl)cyclopropene durch elektrophile Diazoalkan-substitution (1982)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 115 (1982), S. 2965-2980 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Investigations on Diazo Compounds and Azides, XLII. (Diazomethyl)cyclopropenes by Electrophilic Diazoalkane SubstitutionThe (diazomethyl)cyclopropenes 9 and 10 are formed via electrophilic diazoalkane substitution preferably of diazomethylphosphoryl compounds with cyclopropenylium salts. Either the diazomethyl compounds (7a-c) react with the cyclopropenylium salts 6a-e in the presence of triethylamine (method A) or the metallated diazo compounds 8a-d are combined with the cyclopropenylium bromides 6c-e (method B) (details see table 1). The (diazomethyl)cyclopropenes undergo a novel type of isomerization to pyridazines, partly without heating (9d-f → 11b-d), partly by refluxing in toluene (9a,g → 11a,e as well as 10e,f → 12a,b). The bicyclic betaines 15 and 17 are supposed to be intermediates. The diazomethyl compounds 9a and b yield the α,β- unsaturated ketones 20a and b by acid-catalyzed decomposition.
    Notes: Die (Diazomethyl)cyclopropene 9 und 10 entstehen durch elektrophile Substitution vorzugsweise von Diazomethylphosphorylverbindungen mit Cyclopropenyliumsalzen. Man setzt entweder die Diazomethylverbindungen selbst (7a-c) in Gegenwart von Triethylamin mit den Cyclopropenyliumsalzen 6a-e um (Methode A) oder läßt die metallierten Diazoverbindungen 8a-d mit den Cyclopropenyliumbromiden 6c-e reagieren (Methode B) (Details s. Tab. 1). Die (Diazomethyl)-cyclopropene gehen teils ohne Erwärmen (9d-f → 11b-d), teils beim Erhitzen in Toluol (9a,g → 11a,e sowie 10e,f → 12a,b) eine neuartige Isomerisierung zu Pyridazinen ein; Zwischenstufen sind vermutlich die bicyclischen Betaine 15 und 17. Die Diazomethylverbindungen 9a und b liefern bei der säurekatalysierten Zersetzung die α,β-ungesättigten Ketone 20a und b.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19821150904
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  • 2
    Electronic Resource
    Electronic Resource
    Untersuchungen an Diazoverbindungen und Aziden, XXX: C-Alkylierung von Diazomethylphosphorylverbindungen mit Enaminen (1978)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 111 (1978), S. 2290-2296 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Investigations on Diazo Compounds and Azides, XXX: C-Alkylation of (Diazomethyl)phosphoryl Compounds with EnaminesThe phosphoryl diazomethanes 1a and b react with the enamines 2a-d to form the β-amino-α-diazophosphoryl compounds 3a-f. Addition of perchloric acid and hydrogen chloride, respectively, yields the ammonium salts 4a-f. It seems to be plausible, that the alkylation reaction proceeds via the intermediates 5 and 7.
    Notes: Die Phosphoryldiazoalkane 1a und b reagieren mit den Enaminen 2a-d zu den β-Amino-α-diazophosphorylverbindungen 3a-f. Addition von Perchlorsäure bzw. Chlorwasserstoff liefert die Ammoniumsalze 4a-f. Es erscheint plausibel, daß die Alkylierungsreaktion über die Zwischenstufen 5 und 7 verläuft.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19781110624
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  • 3
    Electronic Resource
    Electronic Resource
    Phosphorverbindungen ungewöhnlicher Koordination, 171) über die Abfangreaktion von Phenylthioxophosphan mit Hexacarbonylbis(cyclopentadienyl)dimolybdän (1987)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 120 (1987), S. 1263-1267 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Phosphorus compounds with Unusual Cooradination, 171). - On the Trapping Reaction Of Phenylthioxophosphane with Hexacarbonylbnis(cyclopentadienyl)dimolybdenumPhenylthioxophosphane (6) - generated in boiling toluene from endo/exo-10 - reacts under these conditions with hexacarbonylbis(cyclopentadienyl)dimolybdenum (12) to yield the two binuclear molybdenum complexes 13a and 14a. A crystal structural analysis has been performed for 13a. Lawesson's reagent (17) leads under the same conditions with 12 to the analogous complexes 13b and 14b.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19871200727
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  • 4
    Electronic Resource
    Electronic Resource
    Organophosphorus Compounds, 118Part 2: 117: Ref1. Reactions of 1-Chloro-1H-phosphirenes with Nucleophiles (1997)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 130 (1997), S. 711-723 
    Details
    ISSN: 0009-2940
    Keywords: Phosphorus heterocycles ; 1H-Phosphirenes ; Nucleophilic substitution reactions at 1H-phosphirenes ; Metal-complexation of functionalized 1H-phosphirenes ; Carbonyl complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The halogen atoms in the 1-chloro-1H-phosphirenes, 5a-c, are easily substituted on reaction with organolithium and Grignard reagents, 14a-p, with formation of the corresponding O-, N-, C-, Si-, and Ge-substituted 1H-phosphirenes, 15a-t. C1/H exchange reactions also occur on reaction with lithium metal hydrides (5a → 17). Furthermore, substitution reactions are also realized with the alkali metal borates, 18a-g (→19a-g); the same is true for reactions with trimethylsilyl cyanide and azide (→22a-d). Some of the substitution products have been characterized in the form of their metal complexes, 16, 23, 24, and 25.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19971300607
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  • 5
    Electronic Resource
    Electronic Resource
    Untersuchungen an Diazoverbindungen und Aziden, L1). 7-Brom-5-(diazomethyl)-5H-benzocycloheptatriene - Synthese durch elektrophile Diazoalkansubstitution und Umwandlung in 8-Brombenzocyclooctatetraene (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 3093-3101 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Investigations on Diazo Compounds and Azides, L1). 7-Bromo-5-(diazomethyl)-5H-benzocycloheptatrienes - Syntheses by Electrophilic Diazoalkane Substitution and Transformation into 8-BromobenzocyclooctatetraenesThe benzotropylium bromide 4 undergoes electrophilic diazoalkane substitution with the silver (diazomethyl)phosphoryl compounds 5a-c in dichloromethane to give the 5-(diazomethyl)-5H-benzocycloheptatrienes 6a-c; formation of isomers (4→7) was not observed. Mercury-bis(diazomethylcarbonyl) compounds (8a-d) in benzene react analogously to the 5-(diazomethyl)-5H-benzocycloheptatrienes 9a-d. Copper(II)-acetylacetonate catalyzed decomposition of 6 and 9 in refluxing benzene leads to ring enlargement with exclusive formation of the benzocyclooctatetraenes 12a-f. There is no indication of the simultaneous generation of isomeric reaction products such as 13-16.
    Notes: Das Benzotropylium-bromid 4 geht mit den Silber-(diazomethyl)phosphorylverbindungen 5a-c in Dichlormethan elektrophile Diazoalkansubstitution zu den 5-(Diazomethyl)-5H-benzocycloheptatrienen 6a-c ein; Isomerenbildung (4→7) wurde nicht beobachtet. Quecksilber-bis(diazomethylcarbonyl)verbindungen (8a-d) in Benzol reagieren analog zu den 5-(Diazomethyl)-5H-benzocycloheptatrienen 9a-d. Die Kupfer(II)-acetylacetonat-katalysierte Zersetzung von 6 und 9 in siedendem Benzol führt unter Ringerweiterung ausschließlich zur Bildung der Benzocyclooctatetraene 12a-f. Es gibt keine Hinweise auf das gleichzeitige Entstehen isomerer Reaktionsprodukte wie 13-16.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841171009
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  • 6
    Electronic Resource
    Electronic Resource
    Diazoverbindungen, 70. Intramolekulare Cycloaddition von 5-(Diazomethyl)-5H-benzocycloheptenen - Teilschritt einer neuen Benzosemibullvalen-Synthese (1989)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 122 (1989), S. 565-575 
    Details
    ISSN: 0009-2940
    Keywords: Benzosemibullvalene ; [4 + 3] Cycloaddition ; 5H-Benzocycloheptene, 5-(diazomethyl)- ; Electrophilic diazoalkane substitution ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Diazo Compounds, 701. - Intramolecular Cycloaddition of 5-(Diazomethyl)-5H-benzocycloheptenes - Partial Step of a New Benzosemibullvalene SynthesisElectrophilic diazoalkane substitution of the (diazomethyl)phosphoryl compounds 13a-d with the 7-alkoxybenzocycloheptenylium perchlorates 8a-e yields the 7-alkoxy-5-(diazomethyl)-5H-benzocycloheptenes 15a-l, which generally isomerize quickly by intramolecular cycloaddition to the tetracycles 19a-l. The 7-isomers 14, formed also in the primary substitution process, can be detected by 1H-NMR spectroscopy. By thermal nitrogen elimination, 19a, b, e, and h are transformed into the tetracycles 21a-d. In the case of 19i, k, and l the formation of the tricyclic compounds is accompanied by an additional hetero Cope rearrangement (→22a-c). The reaction of the lithiated diazomethyl compounds 24a and b with 7-morpholinobenzocycloheptenylium perchlorate (23) after chromatographic workup leads to the ketones 26a and b.
    Notes: Elektrophile Diazoalkan-Substitution der (Diazomethyl)phosphoryl-Verbindungen 13a-d mit den 7-Alkoxybenzocycloheptenylium-perchloraten 8a-e liefert die 7-Alkoxy-5-(diazomethyl)-5H-benzocycloheptene 15a-l, die im allgemeinen schnell durch intramolekulare Cycloadditon zu den Tetracyclen 19a-l isomerisieren. Die beim primären Substitutionsprozeß ebenfalls gebildeten 7-Isomeren 14 lassen sich 1H-NMR-spektroskopisch nach-weisen. Durch thermische Stickstoff-Abspaltung werden 19a, b, e und h in die Tetracyclen 21a-d umgewandelt. Im Falle von 19i, k und l ist die Tetracyclen-Bildung noch von einer zusätzlichen hetero-Cope-Umlagerung begleitet (→22a-c). Die Umsetzung der lithiierten Diazomethyl-Verbindungen 24a und b mit 7-Morpholinobenzocycloheptenylium-perchlorat (23) führt nach chromatographischer Aufarbeitung zu den Ketonen 26a und b.
    Additional Material: 7 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19891220327
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  • 7
    Electronic Resource
    Electronic Resource
    Organophosphorverbindungen, 511) Phosphatriafulvene - Phosphaalkene mit inverser Elektronendichte2) (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 2843-2855 
    Details
    ISSN: 0009-2940
    Keywords: Phosphatriafulvenes ; Peterson olefination ; Electron densities, inverse ; 1,3-Diphosphacyclobutanes ; Calculations, ab initio SCF ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Organophosphorus Compounds, 511). - Phosphatriafulvenes - Phosphaalkenes with Inverse Electron Density2)Peterson olefination of the sterically hindered cyclopropenones 1 with the lithium phosphides 2 yields the so far unknown phophatriafulvenes 3 and 4, which possess inverse electron densities. They are characterized by transition metal complex formation (→7, 8). Acylation of 3a with the carboxylic acid chlorides 11 leads to a great variety of P-acylphosphatriafulvenes 13a-s. They partly dimerize under formation of the 1,3-diphosphacyclobutanes 13 ⇌ 14.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911241228
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  • 8
    Electronic Resource
    Electronic Resource
    Bernd Eistert. 1902-1978 (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. XXIX 
    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.19801130302
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  • 9
    Electronic Resource
    Electronic Resource
    Untersuchungen an Diazoverbindungen und Aziden, LV. 7-(Diazomethyl)cycloheptatriene durch elektrophile Diazoalkansubstitution (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 1315-1328 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Investigations on Diazo Compounds and Azides, LV. 7-(Diazomethyl)cycloheptatrienes by Electrophilic Diazoalkane SubstitutionThe silver-(diazomethyl)phosphoryl compounds 2a-c smoothly undergo electrophilic diazo-alkane substitution with 1 to give 3a-c. In contrast, a more complex product formation is encountered in the reaction of 1 with the mercury-bis(diazomethylcarbonyl) compounds 4a-d: Besides the 7-(diazomethyl)cycloheptatrienes 5a-d the styrene derivatives 6a-c as well as the bromomercurio compounds 7a-b are formed. Probably the norcaradiene intermediates 12 and 14 play a role in the formation of 6 and 7. The reaction of the 7-(diazomethyl)cycloheptatrienes 3a-c and 5a, b, d with PTAD (16) affords the [4 + 2]-cycloadducts 17a-f, derived from 7-(diazomethyl)norcaradiene isomers. The structures of 3, 5, and 17 are based above all on 1H and 13C NMR spectroscopic investigations.
    Notes: Die Silber-(diazomethylphosphoryl)-Verbindungen 2a-c gehen mit 1 glatt elektrophile Diazoalkansubstitution zu 3a-c ein. Im Gegensatz dazu begegnet man einem komplexeren Produktbild bei der Umsetzung von 1 mit den Quecksilber-bis(diazomethylcarbonyl)-Verbindungen 4a-d: Neben den 7-(Diazomethyl)cycloheptatriene 5a-d werden die Styrolderivate 6a-c sowie die Brommercurioverbindungen 7a-d gebildet. Die Norcaradienzwischenstufen 12 und 14 spielen vermutlich eine Rolle bei der Bildung von 6 und 7. Mit PTAD (16) liefern die 7-(Diazomethyl)cycloheptatriene 3a-c und 5a, b, d von Norcaradienisomeren abgeleiteten [4 + 2]-Cycloaddukte 17a-f. Die Strukturen von 3, 5 und 17 werden vor allem durch 1H und 13C-NMR-spektroskopische Untersuchungen ermittelt.
    Additional Material: 6 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851180404
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