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