Hypervalent iodine(III)-mediated oxidation of aldoximes to N-acetoxy or N-hydroxy amides

Harisadhan Ghosh; Bhisma K. Patel

doi:10.1039/B917096K

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Organic & Biomolecular Chemistry

Issue 2, 2010

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Hypervalent iodine(III)-mediated oxidation of aldoximes to N-acetoxy or N-hydroxy amides

Harisadhan Ghosh and Bhisma K. Patel

Org. Biomol. Chem., 2010, 8, 384-390

DOI: 10.1039/B917096K
Received 19 Aug 2009, Accepted 25 Sep 2009
First published on the web 26 Oct 2009

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Abstract
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Treatment of various aliphatic and aromatic aldoximes with the hypervalent iodine(III) reagents (diacetoxyiodo)benzene (DIB) or Koser's reagent [hydroxy(tosyloxy)iodo]benzene (HTIB) gave, respectively, N-acetoxy or N-hydroxy amides in good yields rather than the expected nitrile oxide dimerised product oxadiazole-N-oxides reported to be formed with other oxidising and hypervalent iodine reagents. The acetate or the hydroxyl group of DIB or HTIB attacks on the aryl/alkylnitrile oxides formed in situ, which, upon intramolecular rearrangement, gave the expected N-acetoxy or N-hydroxy amides.

Abstract from Methods in Organic Synthesis 2010

Using (diacetoxyiodo)benzene the aryl aldoximes were converted directly into N-acetoxy amides in good yield.

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¹H and ¹³C NMR spectra; X-ray structure for 9a
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Organic & Biomolecular Chemistry

Hypervalent iodine(III)-mediated oxidation of aldoximes to N-acetoxy or N-hydroxy amides

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