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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 4
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Articles

A facile sulfenylchlorination of alkenes with Me2SO/(COCl)2

Liyuan Lan Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University , Beijing, ChinaView further author information
,
Yang Gao Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University , Beijing, ChinaView further author information
,
Rui Ding Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University , Beijing, ChinaView further author information
,
Ting Zhang Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University , Beijing, ChinaView further author information
,
Yongguo Liu Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University , Beijing, ChinaView further author information
,
Baoguo Sun Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University , Beijing, ChinaView further author information
&
Hongyu Tian Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University , Beijing, ChinaCorrespondence[email protected]
View further author information
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Pages 539-549 | Received 01 Oct 2018, Published online: 23 Jan 2019
 
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Abstract

The sulfenylchlorination of a series of alkenes is investigated by using the combined reagent of dimethyl sulfoxide and oxalyl chloride. The corresponding β-chloro sulfides were obtained in mediate to good yields. Most of the terminal alkenes give the Markovnikov adducts mainly and the sulfenylchlorination of cyclic alkenes is stereospecific to produce the adducts with trans configuration. Methanesulfenyl chloride is supposed to be the real species for sulfenylchlorination.

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Funding

Financial support from the National Key Research and Development Program (2016YFD0400801), Beijing Postdoctoral Research Foundation (2017-22-011) and the Importation and Development of High-Caliber Talents Project of Beijing Municipal Institutions (CIT&TCD20140306) is gratefully acknowledged.

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