Cleavage of carbon-carbon bonds. Copper (II)-induced oxygenolysis of o-benzoquinones, catechols, and phenols. On the question of nonenzymic oxidation of …

MM Rogic, TR Demmin

Index: Rogic,M.M.; Demmin,T.R. Journal of the American Chemical Society, 1978 , vol. 100, # 17 p. 5472 - 5487

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Citation Number: 124

Abstract

Abstract: o-Benzoquinones and catechols undergo the carbon-carbon bond cleavages induced by a particular copper (11) reagent in the presence as well as in the absence of molecular oxygen. The overall anaerobic transformation of catechol to cis, cis-muconic acid monomethyl ester involves a two-electron oxidation of catechol to o-benzoquinone, followed by a second twoelectron oxidation of the o-benzoquinone to the muconic acid ester. The ...