Reaction of aromatic aldehydes with 1,2-dibenzylhydrazine

Abstract

The reactions of 1,2-dibenzylhydrazine with several aromatic aldehydes in refluxing toluene gave the benzaldehyde dibenzylhydrazones (9) and (13) in high yield. It is suggested from labelling studies and from the failure to trap an azomethine imine in the reaction between dibenzylhydrazine and benzaldehyde that such intermediates are not involved in the formation of the hydrazones. These products may be formed directly via hydride transfer in the hydrazinocarbinol (18) or the hydrazonium ion (19).