BISMUTH(III)-CATALYZED OXIDATIVE CLEAVAGE OF ARYL EPOXIDES - SUBSTITUENT EFFECTS ON THE KINETICS OF THE OXIDATION REACTION

被引：26

作者：

LEBOISSELIER, V ^{[1
]}

DUNACH, E ^{[1
]}

POSTEL, M ^{[1
]}

机构：

[1] UNIV NICE,FAC SCI,CHIM MOLEC LAB,CNRS,URA 426,F-06108 NICE 2,FRANCE

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1994年 / 482卷 / 1-2期

关键词：

BISMUTH; ARYL EPOXIDE CLEAVAGE; OXIDATION; SUBSTITUENT EFFECTS; BI(III) CATALYSIS; HAMMET CORRELATION;

D O I：

10.1016/0022-328X(94)88192-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Bismuth(III)mandelate catalyzes the oxidative C-C bond cleavage of a series of styrene epoxides in DMSO, to the corresponding aryl carboxylic acids. The reaction is accelerated in the presence of electron-donating groups substituting the phenyl ring. A good Hammet correlation of log k(obs) versus sigma has been obtained, with a rho of - 1.08.

引用

页码：119 / 123

页数：5

共 23 条

[1] A CATALYTIC METHOD FOR ALPHA-GLYCOL CLEAVAGE [J].

BARTON, DHR ;

STOBIE, A ;

MOTHERWELL, WB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (23) :1232-1233

[2] OXIDATION OF ORGANIC SUBSTRATES BY PENTAVALENT ORGANO-BISMUTH REAGENTS [J].

BARTON, DHR ;

LESTER, DJ ;

MOTHERWELL, WB ;

BARROSPAPOULA, MT .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (16) :705-707

[3] THE CHEMISTRY OF PENTAVALENT ORGANOBISMUTH REAGENTS .10. STUDIES ON THE PHENYLATION AND OXIDATION OF PHENOLS [J].

BARTON, DHR ;

YADAVBHATNAGAR, N ;

FINET, JP ;

KHAMSI, J ;

MOTHERWELL, WB ;

STANFORTH, SP .

TETRAHEDRON, 1987, 43 (02) :323-332

[4] THE CHEMISTRY OF PENTAVALENT ORGANOBISMUTH REAGENTS - .9. CLEAVAGE REACTIONS OF ALPHA-GLYCOLS [J].

BARTON, DHR ;

FINET, JP ;

MOTHERWELL, WB ;

PICHON, C .

TETRAHEDRON, 1986, 42 (20) :5627-5636

[5] FUNCTIONAL-GROUP OXIDATION BY PENTAVALENT ORGANOBISMUTH REAGENTS [J].

BARTON, DHR ;

KITCHIN, JP ;

LESTER, DJ ;

MOTHERWELL, WB ;

PAPOULA, MTB .

TETRAHEDRON, 1981, 37 :73-79

[6] EFFECTS OF PARA-SUBSTITUENTS ON THE MECHANISMS OF SOLVOLYSIS OF STYRENE OXIDES [J].

BLUMENSTEIN, JJ ;

UKACHUKWU, VC ;

MOHAN, RS ;

WHALEN, DL .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (04) :924-932

[7]

BRIGGS J, 1971, J CHEM SOC B, P55

[8]

BUCHANAN JB, 1972, SELECTIVE ORGANIC TR, V2

[9] REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .5. SYNTHESIS AND REACTIONS OF SOME 2,3-EPOXY-1-ALKANOL DERIVATIVES [J].

CHINI, M ;

CROTTI, P ;

FLIPPIN, LA ;

GARDELLI, C ;

GIOVANI, E ;

MACCHIA, F ;

PINESCHI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1221-1227

[10] STEROIDAL SAPOGENINS .37. EXPERIMENTS IN THE HECOGENIN SERIES .6. CONVERSION TO CORTISONE [J].

DJERASSI, C ;

RINGOLD, HJ ;

ROSENKRANZ, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (21) :5533-5536

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