Tetrahedron

Oxidation of cycloalkanones with hydrogen peroxide: an alternative route to the Baeyer–Villiger reaction. Synthesis of dicarboxylic acid esters

AO Terent'ev, MM Platonov, AS Kashin, GI Nikishin

Index: Terent'ev, Alexander O.; Platonov, Maxim M.; Kashin, Alexey S.; Nikishin, Gennady I. Tetrahedron, 2008 , vol. 64, # 34 p. 7944 - 7948

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Citation Number: 24

Abstract

The acid-catalyzed oxidation of cycloalkanones C5–C8 and C12 with hydrogen peroxide in alcohols was performed, and dicarboxylic acid esters were obtained as the major products in 53–70% yields. In the first step, geminal bishydroperoxides are generated from five-to- seven-membered cyclic ketones. The Baeyer–Villiger reaction is a side process accompanied by the formation of ω-hydroxycarboxylic acid esters.