On the mechanism of formation of 1,4,5,8-tetrathianaphthalene (TTN) from dimercaptoisotrithione (dmit) derivatives

The mechanism of formation of TTN (an important precursor to tetrathiafulvalene (TTF)) from 4,5-bis(benzoylthio)-1,3-dithiole-2-thione is discussed. Contrary to previous reports, ethylenetetrathiolate is not an intermediate in this synthesis, whereas 4,5-vinylenedithio-1,3-dithiole-2-thione is likely to be. The latter is prepared by a new synthesis and converted into TTN in one step.