COUPLING BETWEEN RADICAL AND ANION IN THE OUTERSPHERE OXIDATION OF ALPHA-SULFONYL CARBANIONS - ITS ROLE ON THE PRODUCT DISTRIBUTION BETWEEN DIMERIC OLEFIN AND DISULFONE

被引：16

作者：

AMATORE, C ^{[1
]}

ELMOUSTAFID, T ^{[1
]}

ROLANDO, C ^{[1
]}

THIEBAULT, A ^{[1
]}

VERPEAUX, JN ^{[1
]}

机构：

[1] ECOLE SUPER PHYS & CHIM IND VILLE PARIS,CHIM & ELECTROCHIM MAT MOLEC LAB,CNRS,URA 429,F-75231 PARIS 05,FRANCE

来源：

TETRAHEDRON | 1991年 / 47卷 / 4-5期

关键词：

D O I：

10.1016/S0040-4020(01)87067-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The electrochemical oxidation of alpha-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 alpha-sulfonyl carbanions is examined.

引用

页码：777 / 789

页数：13

共 39 条

[1] ONLINE COMPENSATION OF OHMIC DROP IN SUBMICROSECOND TIME RESOLVED CYCLIC VOLTAMMETRY AT ULTRAMICROELECTRODES
AMATORE, C
LEFROU, C
PFLUGER, F
[J]. JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1989, 270 (1-2) : 43 - 59
[2] UNEXPECTED SINGLE ELECTRON-TRANSFER CATALYZED CYCLIZATION OF PRENYL SULFONE DIMER - EVIDENCE FOR RADICAL-ANION COUPLING IN THE OUTER-SPHERE OXIDATION OF PRENYL SULFONE CARBANION
AMATORE, C
THIEBAULT, A
VERPEAUX, JN
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (20) : 1543 - 1545
[3] HYDROGEN-ATOM TRANSFER OXIDATION OF PRIMARY AND SECONDARY ALCOHOLATES INTO ALDEHYDES AND KETONES BY AROMATIC HALIDES IN LIQUID-AMMONIA - A NEW ELECTROCHEMICALLY INDUCEIBLE REACTION
AMATORE, C
BADOZLAMBLING, J
BONNELHUYGHES, C
PINSON, J
SAVEANT, JM
THIEBAULT, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (07) : 1979 - 1986
[4] ELECTRON-TRANSFER INDUCED REACTIONS - ELECTROCHEMICALLY STIMULATED AROMATIC NUCLEOPHILIC-SUBSTITUTION IN ORGANIC-SOLVENTS
AMATORE, C
PINSON, J
SAVEANT, JM
THIEBAULT, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (03) : 817 - 826
[5] ANDRIEUX CP, 1986, INVESTIGATION RATE 2, V6, P305
[6] ORGANIC-SYNTHESIS WITH SULFONES .32. A CONVENIENT ROUTE TO ALPHA,BETA-UNSATURATED SULFONES FROM SATURATED SULFONES
BAUDIN, JB
JULIA, M
ROLANDO, C
VERPEAUX, JN
[J]. TETRAHEDRON LETTERS, 1984, 25 (30) : 3203 - 3204
[7] BAUDIN JB, 1987, B SOC CHIM FR, P493
[8] BERDNIKOV EA, 1978, ZH OBSHCH KHIM+, V48, P875
[9] STEREOCHEMISTRY OF FREE-RADICAL ELIMINATIONS ON BETA-PHENYLSULFONYL RADICALS
BOOTHE, TE
GREENE, JL
SHEVLIN, PB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (05) : 794 - 797
[10] EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION
BORDWELL, FG
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) : 456 - 463

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