The Journal of Organic Chemistry

Group transfers. 2. Solvolysis of isopropyl arenesulfonates in sulfolane

BM Jacobson, ES Lewis

Index: Jacobson, Barry M.; Lewis, Edward S. Journal of Organic Chemistry, 1988 , vol. 53, # 2 p. 446 - 447

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Citation Number: 5

Abstract

An attempt was made to study near identity replacements of one isopropyl arenesulfonate with another arenesulfonate anion. Such results would have paralleled the analogous studies of methyl transfers between arenesulfonates, 2 except with an alkyl group more able to tolerate a positive charge in the transition state. This attempt, however, failed. The isopropyl esters in tetrahydrothiophene 1, l-dioxide (sulfolane) are not stable enough to ...