The electrochemical oxidation of silver and tetraethylammonium salts of formamides and imides.N,N-Coupling of formanilidyl radicals
作者:
Jean-Yves Huot,
Denis Serve,
Sylvie Desjardins,
Jean Lessard,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1988)
卷期:
Volume 66,
issue 1
页码: 35-44
ISSN:0008-4042
年代: 1988
DOI:10.1139/v88-005
出版商: NRC Research Press
数据来源: NRC
摘要:
The electrochemical oxidation of [amide-Ag-amide]Ag, [amide-Ag-amide]Et4N, and [amide]Et4N salts of imides and formanilides, in acetonitrile containing tetraethylammonium tetrafluoroborate, at platinum and vitreous carbon electrodes, is a one-electron and irreversible (αn < 1) process leading to an amidyl radicals that preferentially abstracts hydrogen from the medium to give the parent amide.N,N-Coupling (formation of hydrazine derivatives) was observed in the oxidation of the amide-Ag-amide anions of formanilide andp-methoxyformanilide. No coupling was observed in the oxidation of the amide-Ag-amide anion ofp-cyanoformanilide and of imides, and in the oxidation of any of the tetraethylammonium salts (amidyl anions) studied. The formanilidyl radical was trapped byN-tert-butyl-α-phenylnitrone. Attempts to trap the succinimidyl radical by addition to olefins were unsuccessful.
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