Anodic Oxidation of the N-cyanomethyloxazolidine system

The electrochemical oxidation of the N-cyanomethyloxazolidine system in acetonitrile at a platinum electrode afforded a radical cation which might follow either one of two pathways, according to the experimental conditions: the first, in the presence of chloride or bromide ions led to halogenated pr...

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Bibliographic Details
Published in:Tetrahedron 1996-11, Vol.52 (48), p.15127-15136
Main Authors: Billon-Souquet, Florence, Martens, Thierry, Royer, Jacques
Format: Article
Language:English
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Summary:The electrochemical oxidation of the N-cyanomethyloxazolidine system in acetonitrile at a platinum electrode afforded a radical cation which might follow either one of two pathways, according to the experimental conditions: the first, in the presence of chloride or bromide ions led to halogenated products, the second, in the presence of water, led to lactam/amide formation. The mechanistic pathway of both reactions is discussed. The oxidation of 1 afforded a radical cation which might follow either one of two pathways, leading to halogenated products, or to lactam / amide formation.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(96)00947-7