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Photoinduzierte Cycloadditionen von 2,2-Dimethyl-3-phenyl-2H-azirin an Nitrile und "push-pull"-Olefine


Stegmann, Werner; Gilgen, Paul; Heimgartner, Heinz; Schmid, Hans (1976). Photoinduzierte Cycloadditionen von 2,2-Dimethyl-3-phenyl-2H-azirin an Nitrile und "push-pull"-Olefine. Helvetica Chimica Acta, 59(4):1018-1027.

Abstract

Electron deficient nitriles of the type 5a-e in contrast to nonactivated nitriles undergo regiospecific [2+3]cycloadditions to benzonitrile isopropylide (2b), which was generated in situ by irradiation of 2,2-dimethyl-3-phenyl-2H-azirine (1b), to yield the 2H-imidazole derivatives 6a-e (Scheme 2). The structure of the photoproducts was mainly deduced from 13C-NMR and mass spectrometry. Whereas normal olefins or enolethers do not react with 2b, push-pull olefins of the type 10a-d readily undergo the cycloaddition to give the 3-alkoxy-5,5-dimethyl-2-phenyl-1-pyrrolines 11a-d (Scheme 3 and 4). The structure of the photoproducts 11a-d indicates that the regiospecificity of the cycloaddition corresponds to that of acrylonitriles and acrylesters with 2b.

Abstract

Electron deficient nitriles of the type 5a-e in contrast to nonactivated nitriles undergo regiospecific [2+3]cycloadditions to benzonitrile isopropylide (2b), which was generated in situ by irradiation of 2,2-dimethyl-3-phenyl-2H-azirine (1b), to yield the 2H-imidazole derivatives 6a-e (Scheme 2). The structure of the photoproducts was mainly deduced from 13C-NMR and mass spectrometry. Whereas normal olefins or enolethers do not react with 2b, push-pull olefins of the type 10a-d readily undergo the cycloaddition to give the 3-alkoxy-5,5-dimethyl-2-phenyl-1-pyrrolines 11a-d (Scheme 3 and 4). The structure of the photoproducts 11a-d indicates that the regiospecificity of the cycloaddition corresponds to that of acrylonitriles and acrylesters with 2b.

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Additional indexing

Other titles:Photoinduced Cycloadditions of 2,2-DimethyI-3-phenyl-2H-azirine with Nitriles and 'push-pull' Olefines
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1976
Deposited On:05 Nov 2014 11:36
Last Modified:05 Apr 2016 18:28
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung
Publisher DOI:https://doi.org/10.1002/hlca.19760590407

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