Ghosh, Harisadhan ; Patel, Bhisma K. (2010) Hypervalent iodine(III)-mediated oxidation of aldoximes to N-acetoxy or N-hydroxy amides Organic and Biomolecular Chemistry, 8 (2). pp. 384-390. ISSN 1477-0520
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Official URL: http://pubs.rsc.org/en/content/articlelanding/2010...
Related URL: http://dx.doi.org/10.1039/B917096K
Abstract
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 113931 |
| Deposited On: | 30 Apr 2018 12:06 |
| Last Modified: | 30 Apr 2018 12:06 |
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