The Journal of Organic Chemistry

Unsaturated Neopentyl Compounds. The Acetolysis of 2, 2-Dimethyl-3-buten-1-yl and 2, 2, 4-Trimethyl-3-penten-1-yl p-Bromobenzenesulfonates. π-Electron …

RS Bly, RT Swindell

Index: Bly,R.S.; Swindell,R.T. Journal of Organic Chemistry, 1965 , vol. 30, p. 10 - 22

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Citation Number: 21

Abstract

The acetolysis of 2, 2-dimethyl-3-buten-l-y1 p-bromobenzenesulfonate is about 60 times as rapid at 100" as that of 2, 2-dimethylbutyl p-bromobenzenesulfonate, and yields a mixture of 2-methylpentadienes, 2-methyl-4-penten-2-yl acetate, and 4-methyl-3-penten-1-yl acetate. Evidence is presented that this rate enhancement is the result of? r-electron delocalization in the absence of steric strain, and that vinyl is almost as good a" neighboring group" as ...