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Substituent Effect on Reactivity of Alkyl Thiolacetates

Kinetics of catalyzed acyl group exchange between acetic-1-14C anhydride and alkyl thiolacetates was investigated. The exchange is not accompanied by chemical reaction and demonstrates the full equivalency of anhydride acyl groups in the process. The rate of exchange is lowered by increasing branching rather than lengthening in S-alkyl substituents. The role of catalyst and structures of possible intermediates are interpreted. Upon existing linear structure-reactivity relationship a common mechanism involving sulfur atom as the reaction site seems to be operative.