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

Camilla Parmeggiani; Camilla Matassini; Francesca Cardona; Andrea Goti

doi:10.1055/s-0036-1588457

Synthesis, Inhaltsverzeichnis

Synthesis 2017; 49(13): 2890-2900
DOI: 10.1055/s-0036-1588457

special topic

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

Camilla Parmeggiani

^aDipartimento di Chimica ‘Ugo Schiff’, Università degli Studi di Firenze, via della Lastruccia 3–13, 50019 Sesto Fiorentino, Italy

^bCNR-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*

^aDipartimento di Chimica ‘Ugo Schiff’, Università degli Studi di Firenze, via della Lastruccia 3–13, 50019 Sesto Fiorentino, Italy

,

Francesca Cardona

^aDipartimento di Chimica ‘Ugo Schiff’, Università degli Studi di Firenze, via della Lastruccia 3–13, 50019 Sesto Fiorentino, Italy

,

Andrea Goti *

^aDipartimento di Chimica ‘Ugo Schiff’, Università degli Studi di Firenze, via della Lastruccia 3–13, 50019 Sesto Fiorentino, Italy

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

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 - oximes

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Referenzen

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