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  • Isocyanide complexes  (2)
  • Macrocyclic bisdienes and bisdienophiles  (2)
  • Olefins, bis(trifluoromethyl)-substituted  (2)
  • Wiley-Blackwell  (6)
  • American Chemical Society
Collection
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  • Wiley-Blackwell  (6)
  • American Chemical Society
Years
  • 1
    Electronic Resource
    Electronic Resource
    9,10-Phenanthrenocyaninatoeisen(II) (PhcFe) und axial koordinierte Isocyanid-Komplexe (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 1105-1110 
    Details
    ISSN: 0009-2940
    Keywords: 9,10-Phenanthrenocyaninatoiron(II) ; Isocyanide complexes ; Porphyrin derivatives ; Semiconductors, organic ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 9,10-Phenanthrenocyaninatoiron(II) (PhcFe) and Axially Coordinated Isocyanide Complexes9,10-Phenanthrenocyaninatoiron(II) (PhcFe) is synthesized from 9,10-dicyanophenanthrene (3) and pentacarbonyliron. PhcFe exhibits similar spectroscopic properties (UV/VIS and Mößbauer spectra) and similar oxidation potentials as 1,2-Naphthalocyaninatoiron(II) (1,2-NcFe) and Phthalocyaninatoiron(II) (PcFe). Isocyanides RNC (R = tBu, cHx, Bzl, Me2Ph) react with PhcFe to form the corresponding bisaxially substituted 9,10-phenanthrenocyaninatoiron(II) compounds 4-7. Reaction of PhcFe with 1,4-diisocyanobenzene (dib) yields the bridged complex [PhcFe(dib)]n.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230525
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesis of a Bisdienophilic Phthalocyanine and of Precursors for Repetitive Diels-Alder Reactions Based on Hemiporphyrazines and Phthalocyanines (1997)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 130 (1997), S. 801-806 
    Details
    ISSN: 0009-2940
    Keywords: Unsymmetrical phthalocyanines ; Hemiporphyrazines ; Macrocyclic bisdienes and bisdienophiles ; Diels-Alder reactions ; Ladder polymers ; Cycloaddition ; Macrocycles ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The specific synthesis of a metal-free bisdienophilic phthalocyanine 193, suitable for repetitive Diels-Alder reactions, is reported. This was achieved by condensation of 191,3,3-trichloro-6/7-nitroioindolenine (191) and 4,9-dibutoxy-2,3,5,8-tetrahydro-1,3-diimino-1H-5,8-epoxybenz[f]isoindoline (2). The ability of 3 to undergo Diels-Alder reactions was tested by reaction with an excess of 1,2,3,4-tetraphenylcyclopentadienone (5). Experimental data of the hemiporphyrazines 9, 10, and 11, which can be used as precursors for the synthesis of ladder polymers, are also given in the Experimental Section.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19971300620
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  • 3
    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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  • 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 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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  • 6
    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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