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Synthesis 2017; 49(13): 2890-2900
DOI: 10.1055/s-0036-1588457
DOI: 10.1055/s-0036-1588457
special topic
On the Oxidation of Hydroxylamines with o-Iodoxybenzoic Acid (IBX)
Authors
We thank Università degli Studi di Firenze (Fondi di Ateneo) for financial support and Fondazione Donegani/Accademia dei Lincei for a fellowship to C.M.
Weitere Informationen
Publikationsverlauf
Received: 10. April 2017
Accepted after revision: 20. Mai 2017
Publikationsdatum:
07. Juni 2017 (online)
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 - oximesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588457.
- Supporting Information (PDF)
-
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