The Aza-di-π-methane rearrangement of O-acetyl 2,2-dimethyl-4,4-diphenylbut-3-enal oxime

Abstract

The photochemical reaction of O-acetyl 2,2-dimethyl-4,4-diphenylbut-3-enal oxime is described: the reaction yields two cyclopropane derivatives, O-acetyl 3,3-dimethyl-2,2-diphenylcyclopropane carboxaldehyde oxime as the primary photoproduct, formed by an aza-di-π-methane reaction previously unobserved in such compounds, and 1-cyano-3,3-dimethyl-2,2-diphenylcyclopropane formed by thermal elimination of acetic acid from the primary product.