CONTROLLED POTENTIAL ELECTROLYSIS. X. POLAROGRAPHIC BEHAVIOR AND ELECTROLYTIC REDUCTION PROCESS OF ESTERS OF ALIPHATIC ALPHA-NITROCARBOXYLIC ACIDS.

Polarographic reduction mechanism of aliphatic ethyl nitrocarboxylates was investigated. The decrease of the wave height in alkaline region was ascribed to the conversion of the nitro form to aci-nitro anion rather than the ester hydrolysis. Only ethyl nitroacetate developed a wave for the aci-nitro anion. The coulometric n values and the products obtained, combined with the polarographic results, suggest the scheme (1) as the most probable reduction mechanism. The production of amine is only possible through C=N double bond formation, but not through hydroxyamino derivatives as usually suggested.