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13.4.3.2.1 Method 1: By Alkylation of 1,4,2-Dithiazole-5-thiones

DOI: 10.1055/sos-SD-013-00120

Argyropoulos, N. G.Science of Synthesis, (200413103.

In the original synthesis of 1,4,2-dithiazolium salts[‌5‌] a 1,4,2-dithiazole-5-thione 34 is heated with an excess of dimethyl sulfate at 80100°C, followed by treatment of the product with a strong acid. When tetrafluoroboric acid is employed the corresponding 5-(methylsulfanyl)-1,4,2-dithiazolium tetrafluoroborates 35 are formed in yields that range from 24 to 92%. The starting thiones are available either from thiobenzamides and trichloromethanesulfenyl chloride 32,[‌5‌] or from 5-piperidino-1,4,2-dithiazolium salts 33 and hydrogen sulfide (Scheme 9).[‌10‌,‌14‌]

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