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

Year: 2015

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

Autors Affiliation: Dipartimento di Chimica “Ugo Schiff”, Polo Scientifico e Tecnologico, Università di Firenze, Sesto Fiorentino, Italy;
CNR−INO and LENS, Sesto Fiorentino Italy

Abstract: 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.


Volume: 17 (16)      Pages from: 4082  to: 4085

More Information: We thank MIUR-Italy (PRIN 2010-2011, 2010L9SH3K 006) and Universita degli Studi di Firenze (Fondi Ateneo) for financial support. We are grateful to Dr. Francesca Liguori for the preparation of hydroxylamine 13 and its oxidation with different reagents.
DOI: 10.1021/acs.orglett.5b02029

Citations: 47
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