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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 8: 3330 - 3334

DOI: https://doi.org/10.6023/cjoc202102004

NOTES

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

  • Xingyue Wang ,
  • Changlin Xu ,
  • Hongyu Guan ,
  • Mi Lin ,
  • Peng Huang
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  • a College of Chemistry, Liaoning University, Shenyang 110036
    b Dalian (Fushun) Research Institute of Petroleum and Petrochemicals, China Petroleum & Chemical Corporation, Liaoning, Dalian 116045
*Corresponding authors. E-mail: ;
E-mail:

Received date: 2021-02-01

  Revised date: 2021-04-16

  Online published: 2021-05-14

Supported by

Scientific Research Funds of Liaoning Education Department(LYB201606)

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Abstract

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

Cite this article

Xingyue Wang , Changlin Xu , Hongyu Guan , Mi Lin , Peng Huang . Deoxygenation of Sulfoxides with Dimethylthiocarbamoyl Chloride in the Absence of Additional Solvent[J]. Chinese Journal of Organic Chemistry, 2021 , 41(8) : 3330 -3334 . DOI: 10.6023/cjoc202102004

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