Formation of N-Substituted Hydrazones and Azine from Acetone, Ammonia and Amines

Abstract

Acetone azine, which gives hydrazine quantitatively on acid-hydrolysis, was obtained in a high yield from acetone and ammonia via hydrogen peroxide oxidation of the intermediate imine in the presence of benzonitrile. Attempts were made to apply the reaction to the syn-thesis of substituted hydrazones. Thus acetone phenylhydrazone was obtained accompanied with azine from acetone, ammonia and aniline. The yield of phenylhydrazone increased and that of azine decreased with increasing the aniline added. A large excess of aniline was unfavorable for preparation of both azine and hydrazone. Similar behavior was observed for t-butylamine to afford acetone t-butylhydrazone and azine, while cyclohexylamine resulted in the exclusive formation of 2-cyclohexyl-3, 3-dimethyloxaziridine.