Oxidation of Oximes to Nitrile Oxides with Hypervalent Iodine Reagents
Organic Letters2009Vol. 11(7), pp. 1539–1542
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Brian A. Mendelsohn, Shelley Lee, Simon Kim, Florian Teyssier, Virender S. Aulakh, Marco A. Ciufolini
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.
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