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Substituent effects on the photocycloaddition reactions of anisoles to acrylonitriles

✍ Scribed by Nader Al-Jalal; Andrew Gilbert

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
523 KB
Volume
109
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

Methyl‐, ethoxy‐, and phenyl‐substituted acrylonitriles undergo efficient 1,2‐photocyclo‐addition to 4‐cyanoanisole, but the azocine formation of the parent addend is inhibited by these groups. The regiochemistry, selectivity and efficiency of the cycloaddition of acrylonitrile to cyanomethoxyanisoles vary markedly with the position of the arene substituents and reflect competition between the influences of the cyanoanisole and dimethoxybenzene moieties.

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