Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones with Hypervalent Iodine Reagents

Hypervalent iodine compounds are viable reagents for the oxidation of N,N-disubstituted hydroxylamines to the corresponding nitrones, with IBX performing best. The procedure is very simple and user-friendly and affords the target compounds with high efficiency and regioselectivity, highlighting IBX as the reagent of choice for preparation of aldonitrones from nonsymmetric hydroxylamines. Evidence for a mechanism involving nitrogen to iodine coordination has been collected.