Synthesis of 6-Aminobenzopentathiepines by Reactions of 4-Nitrobenzodithiol- 2-ones with NaHS

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.