Decomposition of N,N'-Diacyl-N,N'-dialkoxyhydrazines Revisited

Abstract

N,N′-Diacyl-N,N′-dialkoxyhydrazines have been shown to decompose thermally to esters and nitrogen. An intramolecular crossover experiment has shown that the formation of esters is consistent with a three- centred rearrangement process which is characteristic of N-alkoxy N-amino amides. The four-centred mechanism previously proposed by earlier workers is less favourable energetically. AM1 molecular orbital calculations support these experimental findings.