Nucleophilic addition reaction of aromatic compounds with α-chloroglycidates in the presence of Lewis acid

被引：6
|
作者：
Lin, JR
Gubaidullin, AT
Mamedov, VA
Tsuboi, S [1 ]
机构：
[1] Okayama Univ, Fac Environm Sci & Technol, Dept Environm Chem & Mat, Okayama 7008530, Japan
[2] Russian Acad Sci, AE Arbuzov Organ & Phys Chem Inst, Kazan 420088, Russia
来源：
TETRAHEDRON | 2003年 / 59卷 / 10期
关键词：
Darzens reactions; addition reactions; epoxides; cyclisation;
D O I：
10.1016/S0040-4020(03)00117-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The epoxide 1 obtained by the Darzens condensation reaction of aldehydes with methyl dichloroacetate, reacted with aromatic compounds in the presence of aluminium chloride to afford alpha-aryl-beta-chloro-alpha-hydroxyalkanoate 3. The intra-molecular nucleophilic addition of epoxide 1' gave cyclisation compound 4. The scope and limitation of these reaction were studied for various aldehydes and aromatic compounds. The reaction was also studied in the presence of aluminium chloride supported on alumina or silica gel, which is thought to be a mild Lewis acid and harmless for environment. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1781 / 1790
页数：10
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