Skip to main content
Article
Convenient synthesis of 1,3-dithiolane-2-thiones: cyclic trithiocarbonates as conformational locks
ARKIVOC
  • 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
Document Type
Article
Department
Chemistry
DOI
10.3998/ark.5550190.p008.671
Publication Date
1-1-2014
Disciplines
Abstract
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.
Creative Commons License
Creative Commons Attribution 4.0
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
Available at: http://works.bepress.com/andreas-franz/120/