Selectively synthesis of cyclic di- and trithiocarbonates by N-heterocyclic carbene/LiCl(Br) catalyzed addition of carbon disulfide to epoxides

Carbon disulfide is an abundant, inexpensive and readily available material. One of the main challenges in the reaction of epoxides with CS2 is to control the chemoselectivity as a variety of compounds would be formed in the reaction. A simple and convenient method toward selectively synthesis of ox...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2017-09, Vol.73 (38), p.5706-5714
Main Authors: Mei, Congmin, Li, Xu, Liu, Lihuai, Cao, Changsheng, Pang, Guangsheng, Shi, Yanhui
Format: Article
Language:English
Subjects:
Carbon disulfide
Dithiocarbonate
Epoxide
Trithiocarbonate
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Carbon disulfide is an abundant, inexpensive and readily available material. One of the main challenges in the reaction of epoxides with CS2 is to control the chemoselectivity as a variety of compounds would be formed in the reaction. A simple and convenient method toward selectively synthesis of oxathiolane and trithiocarbonate from epoxides with CS2 catalyzed by NHC/LiCl(Br) under the neat conditions has been developed. This catalytic system exhibits excellent activity and selectivity in cycloaddition reactions of carbon disulfide to terminal epoxides. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.08.009