Journal of the American Chemical Society

Mechanism of carbon-carbon cleavage of cyclic 1, 2-diketones with alkaline hydrogen peroxide. The acyclic mechanism and its application to the basic autoxidation of …

Y Sawaki, CS Foote

Index: Sawaki, Yasuhiko; Foote, Christopher S. Journal of the American Chemical Society, 1983 , vol. 105, # 15 p. 5035 - 5040

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Citation Number: 44

Abstract

Abstract: The reaction of 3, 5-di-tert-butyl-o-benzquinone (3) with alkaline hydrogen peroxide was found to give a considerable amount of methyl ester 5 when H202 was added dropwise. In contrast, the corresponding diacids were not obtained from o-benzoquinone or 1, 2-naphthoquinone on reaction with alkaline H202. An'* O-tracer study of the reaction of 3 and 9, lO-phenanthrenequinone indicated that the CC cleavage reaction proceeds via the ...

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