Addition products of hydrazine derivatives to azo-alkenes - III. α-phenylhydrazino-phenylhydrazones

Abstract

The addition of phenylhydrazine to phenylazo-alkenes 4 yields α-(1-phenylhydrazino)-phenylhydrazones 1 . The reaction of phenylhydrazine with α-halogenated carbonyl compounds 5 affords either 1 or the isomeric α-(2-phenylhydrazino)-phenylhydrazones 2 . Structures 1 and 2 (>N-NH 2 and-NH-NH- groups, respectively) can be differentiated by 1H NMR in DMSO-D 6 solution. Possible pathways of the reactions leading to either 1 or 2 are discussed. Compounds 1 are found to be precursors of phenylosazones 6 .