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)

Autor*innen

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

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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