Oxidation of α-oxo-oximes to nitrile oxides with hypervalent iodine reagents.

J Org Chem

Department of Chemistry, The University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada.

Published: January 2011

AI Article Synopsis

  • The reaction between α-oxo-aldoximes and PhI(OAc)(2) results in the formation of α-oxo-nitrile oxides.
  • α-oxo-ketoximes undergo oxidative cleavage, transforming into nitrile oxides, which can then be trapped by norbornene or styrene with good yields.
  • The reaction is less effective for α,α'-dioxo-ketoximes.

Article Abstract

Upon reaction with PhI(OAc)(2), α-oxo-aldoximes are oxidized to α-oxo-nitrile oxides, while α-oxo-ketoximes are converted into nitrile oxides via the oxidative cleavage of the carbonyl-imino σ bond. The nitrile oxides thus formed were trapped with norbornene or styrene in good yield. α,α'-Dioxo-ketoximes react less efficiently.

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http://dx.doi.org/10.1021/jo102241sDOI Listing

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