The Journal of Organic Chemistry

Selective Mono-O-alkylation of 2, 6-Dibromohydroquinone

LC Dorman

Index: Dorman,L.C. Journal of Organic Chemistry, 1966 , vol. 31, p. 3666 - 3671

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Citation Number: 9

Abstract

It WRS demonstrated that 2, &dibromohydroquinone can be selectively mono-0-alkylated at either the 1 or 4 oxygen depending on whether the monoanion or dianion is being alkylated. The monoanion alkylates preferentially at the I oxygen and the dianion at the 4 oxygen. The selectivity in each case is increased on changing from water to dimethyl sulfoxide and this difference in selectivity is attributed mainly to solvation effects. 2, 6-and 3, 5- ...