Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3330-3334.DOI: 10.6023/cjoc202102004 Previous Articles     Next Articles



王兴越a,b, 许昌林a, 关宏宇a,*(), 林觅a, 黄鹏a,*()   

  1. a 辽宁大学化学院 沈阳 110036
    b 中国石油化工股份有限公司 大连(抚顺)石油化工研究院 辽宁大连 116045
  • 收稿日期:2021-02-01 修回日期:2021-04-16 发布日期:2021-05-14
  • 通讯作者: 关宏宇, 黄鹏
  • 基金资助:

Deoxygenation of Sulfoxides with Dimethylthiocarbamoyl Chloride in the Absence of Additional Solvent

Xingyue Wanga,b, Changlin Xua, Hongyu Guana(), Mi Lina, Peng Huanga()   

  1. a College of Chemistry, Liaoning University, Shenyang 110036
    b Dalian (Fushun) Research Institute of Petroleum and Petrochemicals, China Petroleum & Chemical Corporation, Liaoning, Dalian 116045
  • Received:2021-02-01 Revised:2021-04-16 Published:2021-05-14
  • Contact: Hongyu Guan, Peng Huang
  • Supported by:
    Scientific Research Funds of Liaoning Education Department(LYB201606)

A simple and effective method of sulfoxide deoxidation is reported. Without any additional solvent, a series of aliphatic and aromatic sulfoxides could react with dimethylthiocarbamoyl chloride at 100 ℃ to afford the corresponding thioethers in moderate to excellent yields. This reaction is compatible with a number of functional groups and is suitable for gram-scale synthesis. A mechanism involving the formation of a thiosulfoxide intermediate and its degradation to thioether and elemental sulfur is proposed for the reaction.

Key words: sulfoxide, thioether, deoxygenation, reduction, thionation