Elimination reactions of. beta.-cyano thioethers: evidence for a carbanion intermediate and a change in rate-limiting step

JC Fishbein, WP Jencks

Index: Fishbein, James C.; Jencks, William P. Journal of the American Chemical Society, 1988 , vol. 110, # 15 p. 5075 - 5086

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Citation Number: 28

Abstract

Abstract: The addition reactions of thiol anions to form adducts with acrylonitrile (l), 1- chloroacrylonitrile (2), and fumaronitrile (3) and the corresponding elimination reactions were examined in aqueous solution, generally containing 8.3% Me2S0 at 25 OC. Deuterium exchange into the methanethiol and thiosalicylate adducts of 1 is faster than elimination. Deuterium exchange causes biphasic kinetics for elimination reactions in D20 of the p- ...