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

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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.

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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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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, People’s Republic of China

    Jinsong Cao, Meng Yu, Hanzhu Li, Liang Wang, Xu Zhu, Guangying Wang, Yanhui Shi & Changsheng Cao

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  1. Jinsong Cao
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  2. Meng Yu
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  3. Hanzhu Li
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  4. Liang Wang
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  5. Xu Zhu
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  6. Guangying Wang
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  7. Yanhui Shi
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  8. Changsheng Cao
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Corresponding author

Correspondence to Yanhui Shi.

Additional information

Jinsong Cao and Meng Yu have contributed equally to this work.

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Cao, J., Yu, M., Li, H. et al. Synthesis of cyclic di- and trithiocarbonates from epoxides and carbon disulfide catalyzed by N-heterocyclic carbene. Res Chem Intermed 41, 5323–5330 (2015). https://doi.org/10.1007/s11164-014-1634-5

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