Studies on the scope of the aza-di-π-methane rearrangement of β,γ-unsaturated imines

Abstract

The syntheses of imines of 2,2,4,4-tetraphenylbut-3-enal, 3,3-dimethyl-5,5-diphenylpent-4-en-2-one, and 2,2-dimethyl-1,4,4-triphenylbut-3-en-1-one are described. The results of the irradiation of these and of 2,2-dimethyl-4,4-diphenylbut-3-enonitrile and 2,2-dimethyl-4,4-diphenylbut-3-enal oxime are discussed. The N-isopropyl imine of 2,2,4,4-tetraphenylbut-3-enal and the N-phenyl and benzyl imines of 3,3-dimethyl-5,5-diphenylpent-4-en-2-one undergo the 1-aza-di-π-methane rearrangement.