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Convenient synthesis of 1,3-dithiolane-2-thiones: cyclic trithiocarbonates as conformational locks
  • Irina A. Dotsenko, University of the Pacific
  • Qinliang Zhao, University of the Pacific
  • Andreas H. Franz, University of the Pacific
  • Patrick Batoon, University of the Pacific
  • Nataliya M. Samoshina, University of the Pacific
  • Vyacheslav V. Samoshin, University of the Pacific
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A series of novel 1,3-dithiolane-2-thiones, or cyclic trithiocarbonates, has been prepared by a new simple procedure: a treatment of the corresponding epoxides with the commercially available potassium ethyl xanthogenate, KSC(S)OEt. The stereochemistry of the products was determined by 1 H NMR and in some cases by single-crystal X-ray data. Cyclohexane-based 1,3- dithiolane-2-thiones revealed a trans-fusion of the carbo- and hetero-cycles. The products obtained from the mono-substituted cyclohexene oxides demonstrated an axial position of the substituents. Thus the epoxide transformation into trithiocarbonate can be used as a method for locking cyclic compounds in unstable conformations.
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Citation Information
Irina A. Dotsenko, Qinliang Zhao, Andreas H. Franz, Patrick Batoon, et al.. "Convenient synthesis of 1,3-dithiolane-2-thiones: cyclic trithiocarbonates as conformational locks" ARKIVOC Vol. 2014 Iss. 5 (2014) p. 16 - 41 ISSN: 1551-7012
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