Synthesis and oxidation of some 1-alkenyl-1-phenylhydrazines and their 1,2-isomers

Abstract

The synthesis of a series of 1-alkenyl-1-phenylhydrazines by alkylation of the sodium salt of phenylhydrazine is described, this being found to be the most efficient procedure in terms of the utilisation of the alkylating agent. The oxidative rearrangement of 1-allyl-1-phenylhydrazine to 1-phenylazoprop-2-ene is described, together with the results obtained from the oxidation of other related 1-alkenyl-1-phenylhydrazines. 2-Allyl-1-phenylhydrazine has been synthesised in high yield by alkylating the sodium salt of 1,2-diformyl-1-phenylhydrazine, thus giving an easy route to 1-phenylazoprop-2-ene and other phenylazoalkanes which cannot be prepared via reduction of the corresponding phenylhydrazones.