Journal of the American Chemical Society

Solvolysis of 2-(1-cyclobuten-1-yl) ethyl tosylate

KB Wiberg, JE Hiatt

Index: Wiberg,K.B.; Hiatt,J.E. Journal of the American Chemical Society, 1968 , vol. 90, p. 6495 - 6500

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Citation Number: 8

Abstract

Abstract: The acetolysis of 2-(A1-cyclobutenyl) ethyl tosylate gives 3-methylenecyclopentyl acetate, 2-methylenecyclopentyl acetate, 2-(A1-cyclobuteny1) ethyl acetate, 1- acetoxymethylcyclopentene, and 4-acetoxy-1-methylcyclo-pentene as products. Deuteriumlabeling experiments indicate that a symmetrical spiro [2.3] hexyl-2 cation is not the intermediate. The course of the reaction is discussed.