Tetrahedron letters

Nucleophilic substitution at sulfonyl sulfur atom: Aminolysis of 1-tosyl-3-methyl imidazolium chloride in aqueous medium.

P Monjoint, MF Ruasse

Index: Monjoint, Pierre; Ruasse, Marie-Francoise Tetrahedron Letters, 1984 , vol. 25, # 30 p. 3183 - 3186

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Citation Number: 10

Abstract

Abstract Kinetics of the reaction of 1-tosyl-3-methyl-imidazolium chloride with various amines were measured to examine the nature of sulfonyl transfer in enzymatic reactions. The activation parameters and the value of the brønsted exponent, β= 0.48, are consistent with a small degree of bonding between the entering amine and the sulfur atom in the transition state. Similarities in the nucleophilic behavior of sulfonyl and carbonyl groups ...