The Journal of Organic Chemistry

A mechanistic study of the thermal disproportionation reaction of quinone monoketals

MP Capparelli, JS Swenton

Index: Capparelli, Michael P.; Swenton, John S. Journal of Organic Chemistry, 1987 , vol. 52, # 24 p. 5360 - 5364

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Citation Number: 11

Abstract

Thermolysis of quinone monoketals la4 at 180" C leads to disproportionation to the p- alkoxyphenols 2a-d and the carbonyl compounds derived from the alcohol moiety of the ketal. The thermolysis of 4, 4-dimeth-oxy-2, 5-cyclohexadienone (la) followed first-order kinetics, and the rate of reaction decreased by a factor of 3.6 when the methoxy groups were replaced with methoxy-d3 groups. The suggested mechanism for the reaction involves ...