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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Volume109, Issue1

1990

Pages 21-25

Substituent effects on the photocycloaddition reactions of anisoles to acrylonitriles

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Substituent effects on the photocycloaddition reactions of anisoles to acrylonitriles

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