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

Anno: 2017

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

Affiliazione autori: 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.

Giornale/Rivista: SYNTHESIS-STUTTGART

Volume: 49 (13)      Da Pagina: 2890  A: 2900

Maggiori informazioni: We thank Universita degli Studi di Firenze (Fondi di Ateneo) for financial support and Fondazione Donegani/Accademia dei Lincei for a fellowship to C.M.
Parole chiavi: hypervalent iodine; oxidation; nitrogen; hydroxylamines; nitrones; nitroso dimmers; oximes
DOI: 10.1055/s-0036-1588457

Citazioni: 15
dati da “WEB OF SCIENCE” (of Thomson Reuters) aggiornati al: 2025-05-04
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