Solvents of low nucleophilicity. XII. Triple-bond participation in the acetolysis, formolysis, and trifluoroacetolysis of 6-heptyn-2-yl tosylate and 6-octyn-2-yl tosylate
PE Peterson, RJ Kamat
Index: Peterson,P.E.; Kamat,R.J. Journal of the American Chemical Society, 1969 , vol. 91, p. 4521 - 4527
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Citation Number: 34
Abstract
Abstract: 6-Heptyn-2-yl tosylate and 6-octyn-2-yl tosylate were prepared and solvolyzed. Analysis of the reaction rates and of the products agreed in showing that tripie-bond participation occurred in competition with normal solvolysis, and that the proportion of reaction occurring via a participation path increased as the solvent was varied in the sequence acetic acid, formic acid, and trifluoroacetic acid. 6-Octyn-2-yl tosylate did not ...
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