1,4,2-Dithiazole Explained

1,4,2-Dithiazole is a heterocyclic compound consisting of an unsaturated five-membered ring containing two carbon atoms, one nitrogen atom, and two sulfur atoms. 1,4,2-Dithiazole compounds may be formed by the reaction of nitrile sulfide (formed by the thermolysis of oxathiazolone) with various reactive species;^[1] for instance thiocarbonyls via a 1,3-dipolar cycloaddition reaction.^[2] These compounds may be protonated by strong acids to give synthetically useful aromatic cations.^[3]

Notes and References

1. Argyropoulos. Nikolaos G.. 1,4-Oxa/thia-2-azoles. 1996. 491–543. Comprehensive Heterocyclic Chemistry II. 10.1016/B978-008096518-5.00092-7. 978-0-08-096518-5 .
2. Wai. Kwok-Fai. Sammes. Michael P.. Dithiazoles and related compounds. Part 3. Preparation of 5H-1,4,2-dithiazoles via 1,3-dipolar cycloadditions between nitrile sulphides and thiocarbonyl compounds, and some conversions into 3,5-diaryl-1,4,2-dithiazolium salts. Journal of the Chemical Society, Perkin Transactions 1. 1. 1991. 183. 0300-922X. 10.1039/p19910000183.
3. Wai. Kwok-Fai. Sammes. Michael P.. Dithiazoles and related compounds. Part. 4. Preparation of 1,4,2-dithiazolium salts unsubstituted at C-5 including the parent heterocycle, NMR spectroscopic evidence for aromaticity, and some novel reactions. Journal of the Chemical Society, Perkin Transactions 1. 16. 1992. 2065. 0300-922X. 10.1039/p19920002065.