Mechanistic investigations on the reaction between amines or amides and an alkylperoxy-lambda3-iodane.

J Org Chem

Faculty of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan.

Published: April 2003

A mechanism involving the intermediate formation of an amine radical cation by single-electron transfer is proposed for the oxidation of secondary amines with alkylperoxy-lambda(3)-iodane. On the other hand, the oxidation of acetamides probably proceeds by a radical process, which involves the direct hydrogen abstraction of the methylene group alpha to the nitrogen atom.

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http://dx.doi.org/10.1021/jo0268005DOI Listing

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