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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 22
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Original Articles

Unexpected Formation of O-Acylhydroxamate from the Oxidation of a Dihydroisoquinoline Imine

Hassen Ben Saleh Laboratoire de Chimie des Substances Naturelles, Université de Sfax, Faculté des Science, Sfax, Tunisia
,
Majed Kammoun Laboratoire de Chimie des Substances Naturelles, Université de Sfax, Faculté des Science, Sfax, TunisiaCorrespondence[email protected]
,
Besma Hamdi Laboratoire de Sciences de Matériaux et d'environnement, Université de Sfax, Faculté des Sciences, Sfax, Tunisia
&
Mohamed Damak Laboratoire de Chimie des Substances Naturelles, Université de Sfax, Faculté des Science, Sfax, Tunisia
Pages 3296-3303 | Received 07 Mar 2011, Published online: 18 Jul 2012
 
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Abstract

The reaction of 3,3-dimethyl-7-nitro-3,4-dihydroisoquinoline 1 with m-chloroperbenzoic acid (m-CPBA) mainly yielded oxaziridine and nitrone, with their selectivities being dependent on the solvents. The reaction with 2.5 equivalents of m-CPBA gave small amounts of oxaziridines and hydroxamic acids as well as isolated O-acylhydroxamate compounds.

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