Reactions of cyclohexadienes. Part XIV. Addition reactions of dienamines and electrophilic olefins

Abstract

Treatment of acrylonitrile and of methyl acrylate with the mixture of dienamines [(2) and (3)] obtained by metal-ammonia reduction of N-m-tolylmorpholine gave products corresponding to the presence of different dienes. From this and other evidence it appears that equilibration of isomeric dienamines is brought about by dienophiles. Unlike acrylonitrile and methyl acrylate, which give principally or solely Diels–Alder adducts in several cases investigated, but-1-en-3-one gives a Michael-type adduct.