Benzo-1,3-dithiole-2-thiones reduction

The reduction of benzo-l,2-dithiole-3-thiones (77b) to various polythiols (74ACS(B)827, 63LA(661)84) may be accomplished by lithium (78BEP867155), lithium aluminum hydride, or by catalytic hydrogenation, and Raney nickel hydrodesulfurization gives products by complete elimination of sulfur (B-66MI43100). 

Reduction of l,3-dithiole-2-thione yields an anion-radical (150) whose ESR spectrum at low temperature has been measured the very low proton splitting (indicated in gauss) implies the spin population to be highly concentrated in the trithiocarbonate moiety. Consistent with this, no proton hyperfine splittings were resolved in the ESR spectrum of the anion-radical of benzo-l,3-dithiole-2-thione. ... 

Reduction of l,3-dithiole-2-thione and its benzo-derivative with lithium aluminium hydride gives ethanedithiol and thiocatechol respectively, but similar reduction of the cyclohexene compound (59) replaces the thio-carbonyl group by a methylene group. ... 

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