Extension of the aza-di-π-methane reaction to stable derivatives. Photochemical cyclization of β,γ-unsaturated oxime acetates

Abstract

The successful sensitized photochemical conversion of oxime acetates of some β,γ-unsaturated aldehydes and of one ketone into cyclopropane derivatives by the aza-di-π-methane (ADPM) rearrangement has been carried out. Thus, for example, the acetophenon-sensitized irradiation of the oxime acetate of 2,2-dimethyl-4,4-diphenylbut-3-enal affords the oxime acetate of 2,2-dimethyl-3,3-diphenylcyclopropanecarboxaldehyde in 86% yield and with a quantum yield of 0.12. The first report of the successful ADPM rearrangement with all-alkyl substitution is described.