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Photoinduzierte Cycloadditionen von 2,2-Dimethyl-3-phenyl-2H-azirin an Nitrile und «push-pull»-Olefine. 43. Mitteilung über Photoreaktionen

✍ Scribed by Werner Stegmann; Paul Gilgen; Heinz Heimgartner; Hans Schmid

Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
710 KB
Volume
59
Category
Article
ISSN
0018-019X

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✦ Synopsis

Photoinduced Cycloadditions of 2,2‐Dimethyl‐3‐phenyl‐2__H__‐azirine with Nitriles and ‘push‐pull’ Olefines.

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‐2__H__‐azirine (1b), to yield the 2__H__‐imidazole derivatives 6a–e (Scheme 2). The structure of the photoproducts was mainly deduced from ^13^C‐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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## Abstract Irradiation of 2, 2‐dimethyl‐3‐phenyl‐ (**1a**), 2, 3‐diphenyl‐2__H__‐azirine (**1b**) or the azirine‐precursors 1‐azido‐1‐phenyl‐propene (**2a**) and 1‐azido‐1‐phenyl‐ethylene (**2b**), respectively, in benzene in the presence of azodicarboxylic acid diethylester, yields the correspond