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  • 1
    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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  • 2
    Electronic Resource
    Electronic Resource
    Synthesis of Ladder-Type Oligomers Incorporating Phthalocyanine Units (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 303-311 
    Details
    ISSN: 1434-193X
    Keywords: Phthalocyanines ; Cycloadditions ; Ladder Oligomers ; Macrocycles ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---The condensation of substituted diiminoisoindolines with alkyl-substituted 1,3,3-trichloroisoindolines results in the formation of the highly soluble metal-free phthalocyanines 9, 15. By the same methodology, metal-containing phthalocyanines such as 16, 18 are accessible from suitable metal salts. The precursors 24 and26 were obtained from the phthalocyanine 9 and tetracyclone. The generation of the phthalocyanines 23 and 25 possessing isobenzofuran moieties as diene subunits was accomplished; in the presence of excess 28, the tetracyclone-bisadducts 22 and 24 were transformed into the model compounds 29 and 30, while an excess of 20 or 9 leads to the appropriate trimer-oligomers 31 and 32.
    Type of Medium: Electronic Resource
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  • 3
    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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  • 4
    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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  • 5
    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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