Studies in amine oxide rearrangement:Meisenheimer rearrangement of m-substituted tertiary amine oxides

摘要

A number of N-substituted but-2-ynyl,allyl and 4-aryloxy-2-butynyl-N-methyl anilines 2a-c,3a-h and 5d-f have been synthesized in excellent yield.The m-substituted allylalkylaryl amines have been then treated with one equivalent of m-chloroperoxybenzoic acid (m-CPBA) to give products 9a-h in 80-95% yield.The 4-aryloxy-2-butynyl-N-methyl anilines 5d-f on treatment with m-CPBA proceed through the allene intermediate 7.