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  • 1
    Electronic Resource
    Electronic Resource
    (Tetracyannaphthalocyaninato)eisen(II) mit Isocyaniden als axialen LigandenHerrn Professor Dr. Horst Prinzbach zum 60. Geburtstag gewidmet. (1992)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 1243-1247 
    Details
    ISSN: 0009-2940
    Keywords: (Tetracyanonaphthalocyaninato)iron(II) ; Isocyanide complexes ; Semiconductors ; organic ; Iron complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (Tetracyanonaphthalocyaninato)iron(II) with Isocyanides as Axial Ligands(Tetracyanonaphthalocyaninato)iron(II) [(CN)4-2,3-NcFe; 6] is obtained by treating 2,3,6-tricyanonaphthalene (5) with iron(II) acetate. Compound 5 is synthesized according to the route given in Scheme 1. The mononuclear bisaxial isocyanide complexes (CN)4-2,3-NcFeL2 7-9 with L = tBuNC, cHxNC and AdNC as well as the bridged complex [(CN)4-2,3-NcFe(dib)]n (10) are formed as stable compounds by treating 6 with the neat ligands L. The spectroscopic properties of the complexes are described and compared with the analogous compounds (CN)4PcFeL2, 2,3-NcFeL2, 1,2-NcFeL2, and with PcFeL2. The bridged complex [(CN)4-2,3-NcFe(dib)]n (10) exhibits only poor semiconducting properties as compared to [2,3-NcFe(dib)]n. The oligomer 10 can be doped with iodine, and the resulting product [(CN)4-2,3-NcFe(dib)I1.4]n shows a powder conductivity s̰RT = 2 × 10-5 S/cm at room temperature.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19921250534
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  • 2
    Electronic Resource
    Electronic Resource
    Soluble Substituted μ-Oxo(phthalocyaninato)iron(III) Dimers (1995)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 128 (1995), S. 589-598 
    Details
    ISSN: 0009-2940
    Keywords: μ-Oxobis(phthalocyaninato)iron ; μ-Oxo dimers ; Mössbauer spectroscopy ; Iron complexes ; Phthalocyanines ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Attempts to prepare various peripheral tetra- and octasubstituted (phthalocyaninato)iron derivatives RnPcFe [n = 4: R = CH2OEt (6e), CO2Et (6h), CO2-n-C6H13 (6l), O(2-Et-n-C6H13) (6j), OCH2C(CH3)3 (6k), OCH2C(CH3)2CH2Ph (6l); n = 8: R = CH2CH(CO2Me)CH(CO2Me)CH2 (6f), CH2CH(CO2Et)-CH(CO2Et)CH2 (6g), O-n-C8H17 (6m), O(2-Et-n-C6H13) (6n)] by starting from the corresponding substituted phthalonitriles led to substituted (μ-oxo)bis[(phthalocyaninato)iron(III)] compounds [RnPcFe]2O. The tert-butyl- and ethyl-substituted systems [tBu4PcFe]2O (6c) and [Et4PcFe]2O (6d) were reinve-stigated. UV/Vis, FD mass, Mössbauer, NMR as well as ESR spectroscopy was used to characterize the complexes [RnPcFe]2O to furnish evidence for the presence of Fe-O-Fe moieties in [RnPcFe]2O. The UV/Vis data reported for [RnPcFe]2O as well as their spectral behavior in pyridine correspond to unsubstituted [PcFe]2O. Mössbauer spectra of [RnPcFe]2O show that the complexes were obtained as a mixture of two isomeric μ-oxo compounds A (δFe = 0.22 mm s-1, ΔEQ = 1.33-1.39 mm s-1) and B (ΔFe = 0.33-0.36 mm s-1, ΔEQ = 0.39-0.53 mm s-1), whose Mössbauer parameters are comparable to [PcFe]2O μ-oxo(2) and μ-oxo(1), respectively. Mössbauer spectral data of [RnPcFe]2O indicate high-spin (S = 5/2) FeIII centers. NMR-spectra of [RnPcFe]2O (n = 4: R = tBu, Et, O(2-Et-n-C6H13), OCH2C(CH3)2CH2Ph; n = 8: R = O-n-C8H17, O(2-Et-n-C6H13) give further evidence for μ-oxo bridged structures.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19951280611
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  • 3
    Electronic Resource
    Electronic Resource
    Monomere und überbrückte oligomere (Tetrasulfophthalocyaninato)eisen(II)-Komplexe mit Isocyaniden und N-Donoren als axialen Liganden (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 833-839 
    Details
    ISSN: 0009-2940
    Keywords: Tetrasulfophthalocyaninato ligand ; Iron complexes ; Isocyanide ligands ; Mößbauer spectroscopy, 57Fe ; Semiconductors, organic ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Monomeric and Bridged Oligomeric (Tetrasulfophthalocyaninato)iron(II) Complexes with Isocyanides and N-Donors as Axial Ligands(Tetrasulfophthalocyaninato)iron(II) (TsPcFe) (1) is treated with the isocyanides tert-butyl isocyanide (tBuNC), 1,4-diisocyanobenzene (dib), 2,3,5,6-tetramethyl-1,4-diisocyanobenzene (me4dib), and 4-isocyano-3,5-dimethylpyridine (me2pyNC), and also with pyrazine (pyz) leading to bisaxially coordinated monomers TsPcFe(L)2 (L=tBuNC, dib, me4dib) and the bridged oligomers [TsPcFe(L)]n (L=dib, me4dib, me2pyNC, and pyz). All these complexes are soluble in methanol or water. The spectroscopic properties of the complexes are described, and the average chain lengths of the bridged oligomers are determined by 1H-NMR spectroscopy. The bridged stacked systems exhibit semiconducting properties with and without iodine doping.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240425
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  • 4
    Electronic Resource
    Electronic Resource
    Nickel Hemiporphyrazines as Bisdienes and Bisdienophiles: Synthesis and Characterization (1996)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 129 (1996), S. 237-242 
    Details
    ISSN: 0009-2940
    Keywords: Hemiporphyrazines ; Macrocyclic bisdienes and bisdienophiles ; Nickel complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The bisdienophilic (hemiporphyrazinato)nickel complexes 1a-d bearing various alkoxy groups were synthesized from diiminoisoindoles 9a-d, diaminopyridines 10a, d, and nickel acetate. Reaction of 1a-d with an excess of pentaene 3 delivered the macrocyclic bisdienes 2a-d. The hemiporphyrezines were characterized by 1H- and 13C-NMR spectroscopy. The NMR spectra of the 1,6,16,21-tetrabutoxy-substituted compounds 1b and 2b are discussed with respect to the presence of syn/anti isomers.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19961290220
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  • 5
    Electronic Resource
    Electronic Resource
    Synthese und Charakterisierung neuer Hemiporphyrazinato-Nickelkomplexe (1995)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 128 (1995), S. 417-421 
    Details
    ISSN: 0009-2940
    Keywords: Hemiporphyrazines ; Heminaphthoporphyrazines ; Nickel complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis and Characterization of New Hemiporphyrazinato Nickel ComplexesThe new substituted (hemiporphyrazinato)nickel complexes [HpNi] 3-9 and 11-14, the (heminaphthoporphyrazinato)-nickel complexes 15-19 [HnpNi], and the hemianthraceno-phorphyrazine complex [HapNi] 20 are prepared from isoin-dolenines 1a-e and 10a-d, diaminopyridines 2a-e and nickel acetate. The compounds were characterized by 1H- and 13C-NMR spectroscopy. The 1H-NMR spectrum of the mixture of the 3,18/3,19-substituted (C2v/C2h) complexes is discussed.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19951280414
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  • 6
    Electronic Resource
    Electronic Resource
    Bisaxial koordinierte (Tetraphenylporphinato)eisen(II)-Komplexe (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 841-847 
    Details
    ISSN: 0009-2940
    Keywords: Tetraphenylporphinato ligand ; Iron complexes ; Mößbauer spectroscopy ; 57Fe / Semiconductors, organic ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Bisaxially Coordinated (Tetraphenylporphinato)iron(II) ComplexesThe coordination behavior of (tetraphenylporphinato)iron(II) (TPPFe) has been studied with the preparation of the monomeric complexes TPPFe(L)2 with L=py (pyridine), pyz (pyrazine), 2,6-dimepyz (2,6-dimethylpyrazine), bpy (4,4′-bipyridine), bpyac [1,2-bis(4-pyridyl)acetylene], dabco (1,4-diazabicyclo [2.2.2]octane), and BzINC (benzyl isocyanide). Pure TPPFe has been obtained by thermal decomposition of TPPFe(py)2. The monomeric complexes TPPFe(L)2 with L=pyz, bpy, bpyac, and dabco can be transformed into the bridged systems [TPPFe(L)]n by heating them in toluene or chlorobenzene. The bridged structure of the complexes [TPPFe(L)]n has been confirmed by IR and TG/DTA investigations and especially by Mößbauer spectroscopy. In comparison with the corresponding (phthalocyaninato)iron compounds the bridged TPPFe complexes exhibit lower semi conducting properties even after doping with iodine.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240426
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  • 7
    Electronic Resource
    Electronic Resource
    Synthese und Charakterisierung von substituierten Nickelhemiporphyrazinen (1993)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 1201-1204 
    Details
    ISSN: 0009-2940
    Keywords: Hemiporphyrazines, soluble ; Nickel complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis and Characterization of Substituted Nickel HemiporphyrazinesThe butoxy-substituted (hemiporphyrazinato)nickel compounds (C4H9O)2HpNi (7), (C4H9O)4HpNi (11), and (C4H9O)6HpNi (12) are prepared from isoindolenine 4 or 4,7-dibutoxy-1,3-dihydro-1,3-diiminoisoindole (8), 2,6-diaminopyridines and nickel acetate. The complexes 7, 11, and 12 are soluble in common organic solvents and were characterized by 1H-and 13C-NMR spectroscopy.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19931260521
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  • 8
    Electronic Resource
    Electronic Resource
    Synthese von bis(trifluormethyl)substituierten Pyrethroiden (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 833-845 
    Details
    ISSN: 0170-2041
    Keywords: Pyrethroids ; Olefins, bis(trifluoromethyl)-substituted ; Caronaldehydic acid ethyl ester, hexafluoro- ; Fenvalerate, hexafluoro- ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of Bis(trifluoromethyl)-Substituted PyrethroidsA method for the preparation of 1,1-bis(trifluoromethyl)-substituted pyrethroids is described. For this purpose, 1,1-bis(trifluoromethyl)-substituted olefins 9 are prepared by an easy method from the aldehydes 17 with 2,2-dichlorohexafluoropropane (16) and triphenylphosphine and converted into 2,2-bis(trifluoromethyl)cyclopropanecarboxylates 5a, g, h, i by reacting with (ethoxy-carbonylmethylene)dimethylsulfurane (10). Ethyl 3-formyl-2,2-bis(trifluoromethyl)cyclopropanecarboxylate (hexafluorocaronaldehydic acid ethyl ester) (5c) is obtained from 4,4,4-trifluoro-3-(trifluoromethyl)-2-butenal diethyl acetal (9c) and the sulfurane 10. Compound 5c is an important intermediate in the preparation of the bis(trifluoromethyl)-substituted pyrethroid esters 5d-f. The hydrolysis of the esters 5a, h affords the corresponding carboxylic acids 6a, b which are converted into the pyrethroid esters 7a, b via the acyl chlorides 38 by treating with α-cyano-3-phen-oxybenzyl alcohol (39). 1-(4-Chlorophenyl)-3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (9g) reacts with acetone cyanohydrin to the nitrile 47. The acyl chloride 49 obtained from the nitrile 47 via the carboxylic acid 48 is treated with α-cyano-3-phenoxybenzyl alcohol (39) to form hexafluorofenvalerate (8).
    Notes: Es wird über eine Methode zur Darstellung von 1,1-bis(trifluor-methyl)substituierten Pyrethroiden berichtet. Dazu werden 1,1-bis(trifluormethyl)substituierte Olefine 9 auf einfache Weise durch Reaktion der Aldehyde 17 mit 2,2-Dichlorhexafluorpropan (16) und Triphenylphosphan dargestellt und mit (Ethoxycarbonylmethylen)dimethylsulfuran (10) in die 2,2-Bis(trifluormethyl)cyclo-propancarbonsäureester (5a, g, h, i) übergeführt. Ausgehend von 4,4,4-Trifluor-3-(trifluormethyl)-2-butenal-diethylacetal (9c) wird durch Umsetzung mit dem Sulfuran 10 der 3-Formyl-2,2-bis(trifluormethyl)cyclopropancarbonsäure-ethylester (Hexafluorcaronaldehydsäure-ethylester) (5c) erhalten. 5c stellt eine wichtige Zwischenstufe zur Darstellung der bis(trifluormethyl)substituierten Pyrethroidester 5d-f dar. Die Hydrolyse der Esterfunktion in den Pyrethroidestern 5a, h liefert die Carbonsäuren 6a, b, die über die Säurechloride 38 und Umsetzung mit α-Cyan-3-phenoxy-benzylalkohol (39) in die entsprechenden Pyrethroidester 7a, b übergeführt werden. 1-(4-Chlorphenyl)-3,3,3-trifluor-2-(trifluor-methyl)-1-propen (9g) reagiert mit Aceton-cyanhydrin zum Nitril 47. Nach Überführung in die Carbonsäure 48 und das Säurechlorid 49 wird dieses mit α-Cyan-3-phenoxybenzylalkohol (39) zum Hexafluorfenvalerat (8) umgesetzt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890234
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  • 9
    Electronic Resource
    Electronic Resource
    Synthese von (trifluormethyl)substituierten Pyrethroiden (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 847-852 
    Details
    ISSN: 0170-2041
    Keywords: Olefins, (E)-trifluoromethyl-substituted ; Pyrethroids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of Trifluoromethyl-Substituted Pyrethroids1,1,1-Trifluoroacetone (2) reacts with the phosphorus ylids 1 to give predominantely the (E)-trifluoromethyl-substituted olefins 3a-d. Reaction of 3-trifluoromethyl-2-butenenitrile (3a) with (ethoxycarbonylmethylene)dimethylsulfurane (4a) affords a mixture of four diastereomers of ethyl 3-cyano-2-methyl-2-(trifluoromethyl)cyclopropanecarboxylate (5a). Compound 5a can be reduced by tri-n-hexylsilane to give ethyl 3-formyl-2-methyl-2-(trifluoromethyl)cyclopropanecarboxylate (trifluorocaronaldehydic acid ethyl ester) (6). Monotrifluoromethyl-substituted pyrethroid esters 7a, 7b, and 7c were obtained from the aldehyde 6. Compound 7a is converted into the pyrethroid 7f.
    Notes: 1,1,1-Trifluoraceton (2) reagiert mit den Phosphoryliden 1 zu den (trifluormethyl)substituierten Olefinen 3a-d, wobei überwiegend die E-Isomeren entstehen. 3-(Trifluormethyl)-2-butennitril (3a) wird mit (Ethoxycarbonylmethylen)dimethylsulfuran (4a) zu 3-Cyan-2-methyl-2-(trifluormethyl)cyclopropancarbonsäure-ethylester (5a) umgesetzt, wobei vier Diastereomere entstehen. 5a läßt sich mit Tri-n-hexylsilan zum 3-Formyl-2-methyl-2-(trifluormethyl)cyclopropancarbonsäure-ethylester (Trifluorcaronaldehydsäure-ethylester) (6) reduzieren. Aus dem Aldehyd 6 werden die mono(trifluormethyl)substituierten Pyrethroidester 7a, 7b und 7c gewonnen. 7a wird in das Pyrethroid 7f übergeführt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890235
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  • 10
    Electronic Resource
    Electronic Resource
    Synthese von cis-konfigurierten Bis(trifluormethyl)pyrethroiden (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 1013-1020 
    Details
    ISSN: 0170-2041
    Keywords: Pyrethroids ; Olefins, bis(trifluoromethyl)-substituted ; Caronaldehydic acid methyl ester, hexafluoro- ; Chrysanthemic acid, hexafluoro- ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of cis-Configurated Bis(trifluoromethyl)pyrethroidstrans-2,2-Bis(trifluoromethyl)cyclopropanecarboxylates 2a, b are converted into the cis-diastereomers by base-catalyzed epimerization via the bicyclic lactones 3a, b. Dehydration of cis-2a and cleavage of the ester function leads to the fluorinated chrysanthemic acid 4b, which is converted into the pyrethroids 4d, e. cis-2b is oxidized by pyridinium chlorochromate to give methyl cis-3-formyl-2-2-bis(trifluoromethyl)-cyclopropanecarboxylate (hexafluorocaronaldehydic acid methyl ester) (5). This compound, which is very sensitive to isomerization, is converted into the pyrethroid esters 6a, b predominately retaining the cis configuration; however, by introducing the 2,2-dichlorovinyl side chain the trans diastereomer is obtained. The starting materials trans-2a, b are prepared by the reaction of aldehydes 9a, b with 2,2-dichlorohexafluoropropane and triphenylphosphine followed by cyclopropanization of the resulting 1,1-bis(trifluoromethyl)olefins 10a, b with (ethoxycarbonylmethylene)dimethylsulfurane (14).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1991199101175
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