The Journal of Organic Chemistry

Reactions of Potassium t-Butoxide in Dimethyl Sulfoxide. IV. 1 With Primary Tosylates and Halides*

NF Wood, FC Chang

Index: Wood,N.F.; Chang,F.C. Journal of Organic Chemistry, 1965 , vol. 30, p. 2054 - 2056

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Citation Number: 20

Abstract

When treated with potassium t-butoxide in dimethyl sulfoxide (KtBD) 2 at room temperature, 24-cholanyl tosylate yielded predominantly the t-butyl ether, as might be expected from previous work. a 24-ChIorocholane, however, surprisingly reacted with KtBD to give mainly the elimination product, 23-cholene. The strikingly unexpected difference between tosylate and corresponding chloride led us to investigate further reactions on 2kiodocholane and ...