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Oxidation of Oximes to Nitrile Oxides with Hypervalent Iodine Reagents

Brian A. Mendelsohn, Shelley Lee, Simon Kim, Florian Teyssier, Virender S. Aulakh and Marco A. Ciufolini*

*Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver BC V6T 1Z1, Canada, Email:

B. A. Mendelsohn, S. Lee, S. Kim, F. Tayssier, V. S. Aulakh, M. A. Ciufolini, Org. Lett., 2009, 11, 1539-1542.

DOI: 10.1021/ol900194v

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Iodobenzene diacetate efficiently oxidizes aldoximes to nitrile oxides in MeOH containing a catalytic amount of TFA. Nitrile oxides may be trapped in situ with olefins in a bimolecular or an intramolecular mode. Tandem oxidative dearomatization of phenols/intramolecular nitrile oxide cycloaddition sequences lead to useful synthetic intermediates.

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Key Words

Iodobenzene diacetate, 2-isoxazolines, Huisgen 1,3-Dipolar Cycloaddition

ID: J54-Y2009-1080