Bulletin of the Chemical Society of Japan

SN 2 Reactions in Dipolar Aprotic Solvents. III. Chlorine Isotopic Exchange Reactions of Cinnamyl Chlorides and 3-Aryl-2-propynyl Chlorides. Effect of the …

J Hayami, N Tanaka, A Kaji

Index: Hayami,J.-I. et al. Bulletin of the Chemical Society of Japan, 1973 , vol. 46, p. 954 - 959

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Citation Number: 7

Abstract

Chlorine isotopic exchange reactions of substituted cinnamyl chlorides and 3-aryl-2- propynyl chlorides with tetraethylammonium chloride-36 Cl were studied in acetonitrile. In both cases, the electron-donating groups accelerated the reaction. An acceptable linear Hammett relationship was found for the propynyl chlorides. Cinnamyl chlorides gave a linear relationship for the m-substituted compounds superposed by a concaved U-shaped ...