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Note | Regular issue | Vol 75, No. 8, 2008, pp.1997-2003
Published online, 8th April, 2008
DOI: 10.3987/COM-08-11331
Effects of Aromatic Substituents of Electrochemically Generated Hypervalent Iodine Oxidant on Oxidation Reactions

Yoshiharu Amano and Shigeru Nishiyama*

*Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku Yokohama 223-8522, Japan

Abstract

Phenolic oxidation of 4-hydroxyphenylpropionic acid (5) with electrochemically generated hypervalent iodine oxidant, was performed using a variety of iodobenzene derivatives. Iodobenzene derivatives carrying electron-deficient aromatic moieties showed oxidant activity comparable to that of bis(2,2,2-trifluoroethoxy)phenyliodine(III) 1, and better than those carrying electron-donating groups with the exception of a methyl group. In our electrochemical procedure, the oxidant from 1-iodo-4-nitrobenzene was obtained as a stable solid, while other oxidants that did not precipitate from the reaction mixture, were used in situ. Conversion of the methoxyamide 7 into the corresponding azaspiro derivative 3 was also performed by the oxidants carrying aromkatic substitutions.