Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Controlled Potential Electrolysis. X. Polarographic Behavior and Electrolytic Reduction Process of Esters of Aliphatic α-Nitrocarboxylic Acids
Masaichiro MasuiHiroteru SayoKeiichi Kishi
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1964 Volume 12 Issue 12 Pages 1397-1405

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Abstract
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.
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© The Pharmaceutical Society of Japan
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