Sulfonyl esters. 2. CS cleavage in some substitution reactions of nitrobenzenesulfonates

Sulfonyl esters. 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 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 an...

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Veröffentlicht in:Canadian journal of chemistry 1990-08, Vol.68 (8), p.1450-1455
Hauptverfasser: Baum, James Clayton, Bolhassan, Jimat, Langler, Richard Francis, Pujol, Paul Joseph, Raheja, Raj Kumar
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container_end_page 1455
container_issue 8
container_start_page 1450
container_title Canadian journal of chemistry
container_volume 68
creator Baum, James Clayton
Bolhassan, Jimat
Langler, Richard Francis
Pujol, Paul Joseph
Raheja, Raj Kumar
description 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. Keywords: sulfonyl esters, nitrobenzenesulfonates, CS bond rupture.
doi_str_mv 10.1139/v90-222
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title Sulfonyl esters. 2. CS cleavage in some substitution reactions of nitrobenzenesulfonates
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