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31.13.1.7 Method 7: Diazotization of Anilines Followed by Reaction with Potassium Ethyl Dithiocarbonate

DOI: 10.1055/sos-SD-031-00879

Rakitin, O. A.Science of Synthesis, (200731954.

The traditional nucleophilic aromatic substitution of arenediazonium salts by sulfur functionalities has been known since the 19th century. However, their direct conversion into thiols, by reaction with sodium sulfide, for example, has not been widely employed. A two-step procedure has made this method more widely applicable: as the sulfur nucleophile, metal thiocarboxylate[‌37‌] or, even better, potassium ethyl dithiocarbonate is used (Scheme 8).[‌38‌] The ester 16, formed via the diazo salt 15 from aniline 14, is easily hydrolyzed to give the target arenethiol 17 (Scheme 8).

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