Synthesis of substituted quinones. 2, 5-Disubstituted 1, 4-benzoquinones

HW Moore, YLL Sing, RS Sidhu

Index: Moore, Harold W.; Sing, Yuen-Lung L; Sidhu, Ravinder S. Journal of Organic Chemistry, 1980 , vol. 45, # 25 p. 5057 - 5064

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Citation Number: 18

Abstract

Synthetic methodology is presented which allows the facile synthesis of 2, 5-disubstituted 1, 4-benzoquinones. This involves the initial 1, 2-addition of an alkynyllithium reagent to one of the carbonyl groups of 2, 5-diethoxyor 2, 5-dichloro-3, 6-dimethoxy-1, 4-benzoquinone. This is followed by an analogous addition of an alkyl-, aryl-, or alkynyllithium to the remaining carbonyl to give a cyclohexa-2, 5-diene-1, 4-diol derivative. Acid hydrolysis of these ...