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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 21
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Articles

Dimethyl sulfoxide/oxalyl chloride: A useful reagent for sulfenyletherification

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
,
Siwei ChengBeijing 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 ZhangBeijing 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
,
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
,
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 2773-2781 | Received 13 Aug 2018, Published online: 25 Oct 2018
 
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Abstract

A facile method for the sulfenyletherification of unsaturated alcohols using dimethyl sulfoxide/oxalyl chloride has been described in this article. Methanesulfenyl chloride is supposed to be the compound responsible for the sulfenyletherification, which is generated by the reaction of oxalyl chloride with 2 equivalents of dimethyl sulfoxide. The formation pathway of methanesulfenyl chloride is discussed based on the formation of cyclic acetals.

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Additional information

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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