Reactions of thiourea with chloro-and bromoacetic acids

J Kaválek, S El-Bahaie, V Štěrba

Index: Kavalek, Jaromir; Said-El-Bahaie; Sterba, Vojeslav Collection of Czechoslovak Chemical Communications, 1980 , vol. 45, # 1 p. 263 - 268

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Citation Number: 5

Abstract

Abstract The reaction of chloroacetic acid with thiourea represents an SN 2 substitution of chlorine by sulphur atom and is about two orders of magnitude slower than that of bromoacetic acid. Chloroacetate ion reacts slower than chloroacetic acid only about 30%. The acid catalyzed splitting off of hydroxyl group from the formed tetrahedral intermediate is rate-limiting in the cyclization of the S-carboxylatomethyleneisothiouronium salt, formation ...