Organic & biomolecular chemistry

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

H Ghosh, BK Patel

Index: Ghosh, Harisadhan; Patel, Bhisma K. Organic and Biomolecular Chemistry, 2010 , vol. 8, # 2 p. 384 - 390

Full Text: HTML

Citation Number: 21

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 ...