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

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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

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Publication details

The article was received on 15 May 2018, accepted on 01 Jul 2018 and first published on 02 Jul 2018


Article type: Research Article
DOI: 10.1039/C8QO00481A
Citation: Org. Chem. Front., 2018, Advance Article
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    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, Advance Article , DOI: 10.1039/C8QO00481A

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