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.

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

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