Journal of the American Chemical Society

Photochemical transformations of small ring heterocyclic compounds. 93. Spatial requirements associated with the intramolecular 1, 1-cycloaddition reactions of nitrile …

A Padwa, A Ku

Index: Padwa,A.; Ku,A. Journal of the American Chemical Society, 1978 , vol. 100, p. 2181 - 2190

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Citation Number: 34

Abstract

Abstract: The intramolecular photocycloaddition reactions of a number of o-vinyl, o-allyl, and o-butenylphenyl substituted 2H-azirines have been examined in mechanistic detail. Upon irradiation with ultraviolet light, the o-allylphenyl substituted systems undergo rearrangement to benzobicyclo [3.1. O] hexenes via transient nitrile ylides. Inspection of molecular models of these systems indicates that the normal “two-plane orientation approach” is difficult to ...