A NOVEL REGIOSPECIFIC AND STEREOSPECIFIC HYDROHALOGENATION REACTION OF 2-PROPYNOIC ACID AND ITS DERIVATIVES

被引：154

作者：

MA, S ^{[1
]}

LU, XY ^{[1
]}

LI, ZG ^{[1
]}

机构：

[1] ACAD SINICA,SHANGHAI INST ORGAN CHEM,345 LINGLING LU,SHANGHAI 200032,PEOPLES R CHINA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 02期

关键词：

D O I：

10.1021/jo00028a055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Propynoic acid and its derivatives are hydrohalogenated regio- and stereospecifically by reaction with lithium halides in acetic acid, or preferably with 1 equiv of acetic acid in refluxing CH3CN, to afford the thermodynamically unfavorable (Z)-3-halopropenoic acids and their derivatives as sole products. A rationale for the regio- and stereospecificity is briefly discussed.

引用

页码：709 / 713

页数：5

共 47 条

[41] ADDITIONS TO ACTIVATED CC TRIPLE BOND
WINTERFELDT, E
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (05) : 423 - +
[42] CONFORMATIONAL-ANALYSIS OF SOME N,N-DIMETHYL-BETA-HALOGENOACRYLAMIDES
WOJCIK, J
WITANOWSKI, M
WEBB, GA
[J]. JOURNAL OF MOLECULAR STRUCTURE, 1978, 49 (02) : 249 - 257
[43] WOJCIK J, 1978, B ACAD POL SCI-CHIM, V26, P927
[44] WOJCIK J, 1984, B POL ACAD SCI-CHEM, V32, P85
[45] CONFORMATIONAL-ANALYSIS OF N,N-DIALKYL-BETA-BROMOACRYLAMIDE AND N-MONOALKYL-BETA-BROMOACRYLAMIDES
WOJCIK, J
WITANOWSKI, M
STEFANIAK, L
[J]. JOURNAL OF MOLECULAR STRUCTURE, 1983, 102 (1-2) : 19 - 26
[46] SYNTHESIS OF BICYCLO[2.2.2]OCTENONES VIA INTRA-MOLECULAR DIELS-ALDER REACTIONS OF MODIFIED WESSELY OXIDATION-PRODUCTS
YATES, P
AUKSI, H
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (21): : 2853 - 2863
[47] YOSHIYASA T, 1982, CHEM PHARM BULL, V30, P3167

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