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

Year: 2017

Authors: Parmeggiani C., Matassini C., Cardona F., Goti A.

Autors Affiliation: Univ Firenze, Dipartimento Chim Ugo Schiff, Via Lastruccia 3-13, I-50019 Sesto Fiorentino, Italy; Univ Firenze, European Lab Non Linear Spect, CNR INO, Via Nello Carrara 1, I-50019 Sesto Fiorentino, Italy

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 degrees C furnished oximes as reported, the oxidation in dichloromethane at room temperature afforded efficiently the unusual corresponding nitroso dimers.


Volume: 49 (13)      Pages from: 2890  to: 2900

KeyWords: hypervalent iodine; oxidation; nitrogen; hydroxylamines; nitrones; nitroso dimmers; oximes
DOI: 10.1055/s-0036-1588457

Citations: 14
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