Synthesis and Reactivity of Enantiomerically Enriched Thiiranium Ions

被引：110

作者：

Denmark, Scott E. ^{[1
]}

Vogler, Thomas ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 43期

基金：

美国国家科学基金会;

关键词：

episulfonium ions; Lewis bases; nucleophiles; stereoselectivity; sulfur; ELECTROPHILIC ADDITIONS; THIIRENIUM IONS; SUBSTITUTED THIIRANIUM; EPISELENONIUM ION; SELENIRANIUM IONS; AB-INITIO; ALKENES; SALTS; CARBON; SULFUR;

D O I：

10.1002/chem.200901377

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantiometrically enriched thiiranium ion 5 has been prepared by silver-assisted ionization of chloro sulfide 4 at -20 degrees C. This thiiranium ion is configurationally stable in solution up to room temperature as demonstrated by the stereospecific capture of the ion by various oxygen- and nitrogen-based nucleophiles. Both isolated olefins and weak Lewis bases can promote the racemization of 5 but these processes can also be suppressed at low temperature. Capture of 5 by methanol is faster than the racernization processes.

引用

页码：11737 / 11745

页数：9

共 66 条

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