ACETYLENIC ACIDS .4. REACTIONS OF ALKOXY-SUBSTITUTED PHENYLPROPIOLIC ACIDS AND ESTERS WITH SULFUR HALIDES, PARTICULARLY THIONYL CHLORIDE

被引：16
作者：
BONNIN, CM
CADBY, PA
FREEMAN, CG
WARD, AD
机构：
[1] Department of Organic Chemistry, University of Adelaide, Adelaide, SA, 5001
来源：
AUSTRALIAN JOURNAL OF CHEMISTRY | 1979年 / 32卷 / 04期
关键词：
D O I：
10.1071/CH9790833
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
3, 4-Dialkoxy-substituted phenylpropiolic acids and esters react with thionyl chloride to give good yields of substituted 1-benzothiophen systems. Similar reactions of m- and p-methoxyphenylpropiolic acids and 3, 4, 5-trimethoxyphenylpropiolic acid, which yield mixtures of products, are reported. In contrast, 2, 5- and 2, 3-dimethoxyphenylpropiolic acids gave mixtures in which a coumarin is the major product. The effect of adding pyridine to the reaction mixture is outlined. Reactions involving sulfur monochloride and sulfur dichloride generally gave much lower yields of these products. Attempts to form organometallic intermediates from the 3-chloro-1-benzothiophen products were unsuccessful. © 1979, CSIRO. All rights reserved.
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页码：833 / 847
页数：15
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