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Research on Chemical Intermediates

, Volume 41, Issue 8, pp 5323–5330 | Cite as

Synthesis of cyclic di- and trithiocarbonates from epoxides and carbon disulfide catalyzed by N-heterocyclic carbene

  • Jinsong Cao
  • Meng Yu
  • Hanzhu Li
  • Liang Wang
  • Xu Zhu
  • Guangying Wang
  • Yanhui Shi
  • Changsheng Cao
Article

Abstract

The synthesis of cyclic di- and trithiocarbonates from the reaction of epoxides and carbon disulfide catalyzed by N-heterocyclic carbene prepared in situ is described. 1,3-Oxathiolane-2-thiones or 1,3-dithiolane-2-thiones was obtained in high yield with good selectivity when the reactions were carried out with 4 in DMSO at 100 °C in the presence of K2CO3. The possible catalytic mechanism was proposed.

Graphical Abstract

Keywords

N-Heterocyclic carbene Carbon disulfide Epoxide Dithiocarbonate Trithiocarbonate 

Notes

Acknowledgments

We are grateful to the National Innovative Entrepreneurial Training Programs for Undergraduates (12ssjcxzd02, HXKYZD201203 and 201310320047) of Jiangsu Normal University and PAPD for financial support.

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Copyright information

© Springer Science+Business Media Dordrecht 2014

Authors and Affiliations

  • Jinsong Cao
    • 1
  • Meng Yu
    • 1
  • Hanzhu Li
    • 1
  • Liang Wang
    • 1
  • Xu Zhu
    • 1
  • Guangying Wang
    • 1
  • Yanhui Shi
    • 1
  • Changsheng Cao
    • 1
  1. 1.School of Chemistry and Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional MaterialsJiangsu Normal UniversityXuzhouPeople’s Republic of China

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