'Metal ion electrophilic catalysis' in ring-opening reactions of 1,2-epoxides by metal halides in ionic liquids

被引：11

作者：

Betti, Cecilia

Landini, Dario

Maia, Angelamaria

机构：

[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

[2] Ist CNR, ISTM, I-20133 Milan, Italy

来源：

SYNLETT | 2006年 / 09期

关键词：

epoxides; vic-halohydrins; oxirane ring-opening; ionic liquids; metal ion catalysis;

D O I：

10.1055/s-2006-941562

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Metal ion electrophilic catalysis (Li+ > Na+ >> K+) has been found in ring-opening reactions of 1,2-epoxides 1-5 by metal halides MHal in ionic liquids. The results have been rationalized on the basis of a transition state where the cation M+ stabilizes the negative charge developing on the oxygen atom of the oxirane ring while favoring the nucleophilic attack at the adjacent carbon by the ion-paired anion Hal(-).

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收藏

页码：1335 / 1338

页数：4

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