The reactions of benzodithiol-2-ones containing a 4-nitro group with NaHS led to mixtures of 6- aminobenzopentathiepines and 4-nitrobenzotrithiols. The product ratio and yields depend on the substituent in the aromatic ring. Based on the yields of benzopentathiepines, the following series of substituent efficiency can be inferred: CF3 > > F, Cl > CN. Aminobenzopentathiepines are probably formed via the intermediate benzotrithiols; the transformation apparently starts with the reduction of the nitro group.
Keywords: Benzodithiol, benzopentathiepine, benzotrithiole, pentathiepine, mechanism, trithiole, (trifluoromethyl)benzene, chloro, NaHS, trifluoromethyl
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