Oxidation of oximes to nitrile oxides with hypervalent iodine reagents

…, S Lee, S Kim, F Teyssier, VS Aulakh, MA Ciufolini

Index: Mendelsohn, Brian A.; Lee, Shelley; Kim, Simon; Teyssier, Florian; Aulakh, Virender S.; Ciufolini, Marco A. Organic Letters, 2009 , vol. 11, # 7 p. 1539 - 1542

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Citation Number: 131

Abstract

Iodobenzene diacetate in MeOH containing a catalytic amount of TFA efficiently oxidizes aldoximes to nitrile oxides. The latter may be trapped in situ with olefins in a bimolecular or an intramolecular mode. The new method enables the execution of tandem oxidative dearomatization of phenols/intramolecular nitrile oxide cycloaddition sequences leading to useful synthetic intermediates.