On the Oxidation of Hydroxylamines with o-Iodoxybenzoic Acid (IBX)

Published as part of the Special Topic Modern Strategies with Iodine in Synthesis

Abstract

o-Iodoxybenzoic acid (IBX) is confirmed as a powerful tool for the oxidation of hydroxylamines. The synthetic route is demonstrated as efficient and user friendly, and is exploited on various carbohydrate-derived N,N-disubstituted hydroxylamines (cyclic, acyclic, and functionalized ones), affording the corresponding nitrones in good yields and regioselectivity. N-Monosubstituted hydroxylamines revealed an interesting divergent behavior depending on the reaction conditions. While IBX oxidation in dimethyl sulfoxide at 45 °C furnished oximes as reported, the oxidation in dichloromethane at room temperature afforded efficiently the unusual corresponding nitroso dimers.

Key words

hypervalent iodine - oxidation - nitrogen - hydroxylamines - nitrones - nitroso dimmers - oximes

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