Journal
TETRAHEDRON
Volume 64, Issue 34, Pages 7944-7948Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.06.027
Keywords
oxidation; hydrogen peroxide; cycloalkanones; dicarboxylic acids; bishydroperoxides
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The acid-catalyzed oxidation of cycloalkanones C-5-C-8 and C-12 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 omega-hydroxycarboxylic acid esters. (C) 2008 Elsevier Ltd. All rights reserved.
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