Synthesis 2017; 49(13): 2890-2900
DOI: 10.1055/s-0036-1588457
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Camilla Parmeggiani
a  Dipartimento di Chimica ‘Ugo Schiff’, Università degli Studi di Firenze, via della Lastruccia 3–13, 50019 Sesto Fiorentino, Italy
b  CNR-INO @ European Laboratory for Non Linear Spectroscopy, Università degli Studi di Firenze, via Nello Carrara 1, 50019 Sesto Fiorentino, Italy   Email: andrea.goti@unifi.it   Email: camilla.matassini@unifi.it
,
Camilla Matassini*
a  Dipartimento di Chimica ‘Ugo Schiff’, Università degli Studi di Firenze, via della Lastruccia 3–13, 50019 Sesto Fiorentino, Italy
,
Francesca Cardona
a  Dipartimento di Chimica ‘Ugo Schiff’, Università degli Studi di Firenze, via della Lastruccia 3–13, 50019 Sesto Fiorentino, Italy
,
a  Dipartimento di Chimica ‘Ugo Schiff’, Università degli Studi di Firenze, via della Lastruccia 3–13, 50019 Sesto Fiorentino, Italy
› Author Affiliations
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.
Further Information

Publication History

Received: 10 April 2017

Accepted after revision: 20 May 2017

Publication Date:
07 June 2017 (eFirst)

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.

Supporting Information

 
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