An attempt to explore aromatic sulfonate esters as agents for the condensation of alcohols with mercaptans revealed an unusual process for sulfonate esters: CS bond rupture. Two mechanistic possibilities for CS bond rupture are explored: (i) radical anion intermediacy via single electron transfer and (ii) nucleophilic aromatic substitution. Both experiments and molecular orbital computations are presented to support the conclusion that nucleophilic aromatic substitutions are occurring.Key words: sulfonyl esters, nitrobenzenesulfonates, CS bond rupture.
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.
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