Anionic [3,3], [2,3] and [1,2] rearrangements of aliphatic and aromatic acyl hydrazines with N-N bond cleavage

Article abstract of DOI:10.1016/S0040-4039(97)00320-1

N-Acyl-N'-phenylhydrazines rearrange under basic conditions to afford α-aminophenylacetamides. This reaction can be rationalized in terms of [3,3] sigmatropic shifts of enolized intermediates. The Sommelet-Hauser-type and Stevens-type rearrangements of both aromatic and aliphatic acylhydrazines compete with the [3,3] rearrangement.