OXIDATION OF 2-CHLOROETHYL SULFIDES TO SULFOXIDES BY DIMETHYL-SULFOXIDE

被引：24

作者：

HSU, FL ^{[1
]}

SZAFRANIEC, LL ^{[1
]}

BEAUDRY, WT ^{[1
]}

YANG, YC ^{[1
]}

机构：

[1] USA,CTR CHEM RES DEV & ENGN,RES & PHYS PROTECT DIRECTORATES,ABERDEEN PROVING GROUND,MD 21010

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 13期

关键词：

D O I：

10.1021/jo00300a036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

While most organic sulfides were not oxidized by dimethyl sulfoxide (DMSO), the alkyl 2-chloroethyl sulfides and bis (2-chloroethyl) sulfide slowly reacted with DMSO to produce the corresponding sulfoxides at 25–70 °C under nitrogen. The mechanism of the oxidation is proposed to involve nucleophilic substitution by DMSO followed by neighboring sulfur participation to form a transient sulfonium ion with a four-membered ring structure. The sulfonium ion intermediate rapidly reacts with the chloride ion to produce 2-chloroethyl sulfoxides. 2-Hydroxyethyl sulfoxides were also produced, probably due to the presence of a trace amount of water in the DMSO. This reaction demonstrates, for the first time, the unique reactivity of 2-chloroethyl sulfides in DMSO. © 1990, American Chemical Society. All rights reserved.

引用

页码：4153 / 4155

页数：3

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