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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 20
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Articles

The oxysulfenylation of alkenes with dimethyl sulfoxide/oxalyl chloride

Yongguo LiuBeijing 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 GaoBeijing 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
,
Zhitong WangBeijing 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
,
Jian DongBeijing 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 DingBeijing 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 SunBeijing 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 TianBeijing 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 2662-2670 | Received 22 Feb 2019, Published online: 15 Jul 2019
 
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Abstract

A convenient method for the oxysulfenylation of alkenes using dimethyl sulfoxide/oxalyl chloride is described. Cycloalkenes give trans-adducts stereospecifically. The reactions of styrene are highly regioselective for Markovnikov adducts, whereas aliphatic alkenes lead to anti-Markovnikov adducts mainly.

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Additional information

Funding

Financial support from the National Key Research and Development Program [2016YFD0400801] and Beijing Postdoctoral Research Foundation [2017-22-011].

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