Reduction of ethyl t-cinnamates by Samarium diiodide

被引：5

作者：

Lin, TY ^{[1
]}

Fuh, MR ^{[1
]}

Chan, IS ^{[1
]}

机构：

[1] Soochow Univ, Dept Chem, Taipei, Taiwan

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2001年 / 48卷 / 05期

关键词：

samarium diiodide; ethyl cinnamates;

D O I：

10.1002/jccs.200100121

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Rate constants directly measured from the GC-analyzed method for SmI2 reduction of ethyl t-cinnamate and its substituted derivatives in the presence of HMPA and t-butanol were obtained. HMPA exhibits a stronger catalytic effect than t-butanol. Dependence of reaction rates on concentration of SmI2 and temperature were studied. Electron-donating groups retard this reduction; the electron-withdrawing, groups, on the other hand, enhance the reaction rates dramatically.

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页码：843 / 847

页数：5

相关论文

共 33 条

[1] REACTIONS OF COMPLEX METAL-HYDRIDES OF COPPER WITH ALKYL-HALIDES, ENONES, AND CYCLIC KETONES [J].

ASHBY, EC ;

LIN, JJ ;

GOEL, AB .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (02) :183-188

[2]

ASHBY EC, 1939, J ORG CHEM, V41, P1939

[3]

Brandukova NE., 1994, RUSS CHEM REV, V63, P345

[4] SIMPLIFIED, ONE-POT PROCEDURE FOR THE SYNTHESIS OF [(PH3P)CUH]6, A STABLE COPPER HYDRIDE FOR CONJUGATE REDUCTIONS [J].

BRESTENSKY, DM ;

HUSELAND, DE ;

MCGETTIGAN, C ;

STRYKER, JM .

TETRAHEDRON LETTERS, 1988, 29 (31) :3749-3752

[5] APPROXIMATE ABSOLUTE RATE CONSTANTS FOR THE REACTIONS OF TRIBUTYLTIN RADICALS WITH ARYL AND VINYL HALIDES [J].

CURRAN, DP ;

JASPERSE, CP ;

TOTLEBEN, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25) :7169-7172

[6] THE SAMARIUM GRIGNARD REACTION - INSITU FORMATION AND REACTIONS OF PRIMARY AND SECONDARY ALKYLSAMARIUM(III) REAGENTS [J].

CURRAN, DP ;

TOTLEBEN, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6050-6058

[7]

CURRAN DP, 1992, SYNLETT, P943

[8] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .1. [J].

CURRAN, DP .

SYNTHESIS-STUTTGART, 1988, (06) :417-439

[9] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .2. [J].

CURRAN, DP .

SYNTHESIS-STUTTGART, 1988, (07) :489-513

[10] NEW SEQUENTIAL CARBON-CARBON BOND FORMING REACTIONS - A SAMARIUM(II) IODIDE MEDIATED VINYLOGOUS BARBIER REACTION FOLLOWED BY AN ALDOL REACTION [J].

CURRAN, DP ;

WOLIN, RL .

SYNLETT, 1991, (05) :317-318

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