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Paper | Regular issue | Vol 24, No. 6, 1986, pp.1641-1645
Published online, 1st January, 1970
DOI: 10.3987/R-1986-06-1641
Hypervalent Iodine Oxidation of Flavonols Using [Hydroxy(tosyloxy)iodo]benzebe in Methanol

Robert M. Moriarty,* Om Prakash, Hikmat A. Musallam, and Vijendra K. Mahesh

*Department of Chemistry, University of Illinois at Chicago, 845 West Taylor St., Chicago, IL 60607-7061, U.S.A.

Abstract

Hypervalent iodine oxidation of various flavonols (1a-1f) and α-naphthoflavonol (3) using [hydroxy(tosyloxy)iodo]benzene (HTIB) in methanol leads to the formation of 2,3-dimethoxy-3-hydroxyflavanones (2a-2f) and 2,3-dimethoxy-3-hydroxy-α-naphthoflavanone (4) respectively. HTIB resembles periodic acid in its oxidative behavior towards flavonols.