DECOMPOSITION OF N,N'-DIACYL-N,N'-DIALKOXYHYDRAZINES REVISITED

N,N'-Diacyl-N,N'-dialkoxyhydrazines have been shown to decompose therm ally to esters and nitrogen. An intramolecular crossover experiment ha s shown that the formation of esters is consistent with a three-centre d rearrangement process which is characteristic of N-alkoxy N-amino am ides. The four-centred mechanism previously proposed by earlier worker s is less favourable energetically. AM1 molecular orbital calculations support these experimental findings.