The Journal of Organic Chemistry

Aryl participation in the solvolysis of some gem-dimethyl-substituted 4-aryl-1-alkyl p-bromobenzenesulfonates

S Winstein, RF Heck

Index: Winstein,S.; Heck,R.F. Journal of Organic Chemistry, 1972 , vol. 37, p. 825 - 836

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Citation Number: 11

Abstract

A series of 4-phenyl and 4-anisyl-1-butyl p-bromobenzenesulfates with 3, 3-and 4, Cdimethyl groups was prepared, and acetolysis and formolysis rates were measured. The gem-dimethyl group can appreciably increase the tendency for aryl participation to occur in the solvolysis of these derivatives. Participation by both the 1-and 2 (6)-carbon atoms of the aroqatic ring is observed depending upon the substituents present. The formolysis of 4-(m ...

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