Reaction of lead tetra-acetate with aldehyde nitrophenylhydrazones

Abstract

Oxidation of aliphatic aldehyde 2-nitrophenyl- or 2,4-dinitrophenyl-hydrazones with lead tetra-acetate is exceptional, giving azo-acetates containing α-hydrogen atoms as major products. Lesser yields of the expected diacylhydrazine products are also formed in a competing reaction. The yields of these diacylhydrazines increase, at the expense of the azo-acetates, with increasing chain length of the aliphatic substituent at the methine carbon atom of the hydrazone. Aliphatic aldehyde 4-nitrophenylhydrazones and benzaldehyde 2-nitro- and 2,4-dinitrophenylhydrazones behave normally, giving diacylhydrazines.