Convenient synthesis of 1,3-dithiolane-2-thiones: cyclic trithiocarbonates as conformational locks

Authors

Irina A. Dotsenko, University of the Pacific
Qinliang Zhao, University of the PacificFollow
Andreas H. Franz, University of the PacificFollow
Patrick Batoon, University of the Pacific
Nataliya M. Samoshina, University of the Pacific
Vyacheslav V. Samoshin, University of the PacificFollow

Document Type

Article

Publication Title

ARKIVOC

Department

Chemistry

ISSN

1551-7012

Volume

2014

Issue

5

DOI

10.3998/ark.5550190.p008.671

First Page

16

Last Page

41

Publication Date

1-1-2014

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

This work is licensed under a Creative Commons Attribution 4.0 International License.

Recommended Citation

Dotsenko, I. A., Zhao, Q., Franz, A. H., Batoon, P., Samoshina, N. M., & Samoshin, V. V. (2014). Convenient synthesis of 1,3-dithiolane-2-thiones: cyclic trithiocarbonates as conformational locks. ARKIVOC, 2014(5), 16–41. DOI: 10.3998/ark.5550190.p008.671
https://scholarlycommons.pacific.edu/cop-facarticles/127