Dimethyl sulfoxide/oxalyl chloride: A useful reagent for sulfenyletherification. Issue 21 (2nd November 2018)

• Record Type: Journal Article
• Authors: Gao, Yang; Cheng, Siwei; Zhang, Ting; Ding, Rui; Liu, Yongguo; Sun, Baoguo; Tian, Hongyu
• Is Part Of: Synthetic communications. Volume 48:Issue 21(2018)
• Page Start: 2773
• Page End: 2781
• Publication Date: 2018-11-02
• Subjects: Dimethyl sulfoxide -- methanesulfenyl chloride -- oxalyl chloride -- sulfenyletherification -- unsaturated alcohols; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2018.1524495
• Languages: English
• ISSNs: 0039-7911

Abstract

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. Graphical Abstract: