ChemInform Abstract: Sulfonyl Esters. Part 2. CS Cleavage in Some Substitution Reactions of Nitrobenzenesulfonates.

Abstract

1991 cleavage reactions, decomposition reactions, pyrolysis cleavage reactions, decomposition reactions, pyrolysis O 0100 04 -098 Sulfonyl Esters. Part 2. CS Cleavage in Some Substitution Reactions of Nitrobenzenesulfonates. -An attempt to explore aromatic sulfonate esters as agents for the condensation of alcohols with mercaptans reveal an unusual process for sulfonate esters such as (I): CS-bond rupture to give the sulfide (III) . Two mechanistic possibilities for CS-bond rupture are explored: 1) radical anion intermediacy via single electron transfer and 2) nucleophilic aromatic substitution. Both experiments and MO computations are presented to support the conclusion that nucleophilic aromatic substitution occurs. -(BAUM, J. C.; BOLHASSAN, J.; LANGLER, R. F.; PUJOL, P. J.; RAHEJA, R. K.; Can.