Tetrahedron p. 777 - 789 (1991)
Update date:2022-08-05
Topics:
Amatore
El Moustafid
Rolando
Thiebault
Verpeaux
The electrochemical oxidation of α-sulfonyl carbanions is shown to involve a coupling reaction between the electrogenerated radical and the parent anionic species, both on preparative and kinetic grounds. Two routes compete for the further evolution of the ensuing anion radical: (i) a two step desulfonylation leading to the dimeric olefin, the product of an overall catalytic process, (ii) or further oxidation leading to the dimeric disulfone. Relevance of this mechanism to transition metal oxidations of α-sulfonyl carbanions is examined.
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(1990)