Issue 15, 2018

Green carbon disulfide surrogate via a combination of potassium sulfide and chloroform for benzothiazine-thione and benzothiazole-thione construction

Abstract

An efficient and green carbon disulfide surrogate via facile combination of potassium sulfide and chloroform has been developed. A variety of benzothiazine-thiones and benzothiazole-thiones were straightforwardly established along with the formation of five new chemical bonds in one pot from readily available starting materials, in which the widely used 2-mercaptobenzothiazole (MBT) was synthesized through this method in gram scale. Dichlorocarbene was demonstrated to be a carbon source intermediate from chloroform on the basis of control experimental studies. Meanwhile, potassium sulfide, as a trisulfur radical anion (S3˙) source, was confirmed through UV-visible spectroscopy and an EPR study.

Graphical abstract: Green carbon disulfide surrogate via a combination of potassium sulfide and chloroform for benzothiazine-thione and benzothiazole-thione construction

Supplementary files

Article information

Article type
Research Article
Submitted
15 mai 2018
Accepted
01 jul 2018
First published
02 jul 2018

Org. Chem. Front., 2018,5, 2390-2394

Green carbon disulfide surrogate via a combination of potassium sulfide and chloroform for benzothiazine-thione and benzothiazole-thione construction

W. Tan, C. Wang and X. Jiang, Org. Chem. Front., 2018, 5, 2390 DOI: 10.1039/C8QO00481A

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