Functionally substituted sulfur-containing compounds 12. Reactions of 2-[(organylthio)methyl] oxiranes with aliphatic alcohols in the presence of boron trifluoride etherate

被引：1

作者：

Kalugin, VE ^{[1
]}

Litvinov, VP ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 117913, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2000年 / 49卷 / 05期

关键词：

2-[(organylthio)methyl]oxiranes; aliphatic alcohols; boron trifluoride etherate; isomers; steric factor; thiiranium intermediate;

D O I：

10.1007/BF02494713

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reactions of 2-[(organylthio)methyl]oxiranes with aliphatic alcohols in the presence of catalytic amounts of BF3. Et2O are accompanied by 1,2-migration of the oganylthio group to give mixtures of 2-alkoxy-3-(organylthio)propan-1-ols and 3-alkoxy-2-(organylthio)propan-1-ols. The ratio of these isomers is significantly influenced by the structure of the alcohol and the nature of the organylthio group. The proposed reaction mechanism includes the formation of a thiiranium intermediate and its subsequent transformations.

引用

页码：879 / 885

页数：7