Umpolung of the 5-Alkyl-2-dimethylamino-1,3-dithiolium-4-thiolate Mesoion and Its Application in the Synthesis of Some New Tetrathiafulvalenes

The 5-alkyl-2-dimethylamino-1,3-dithiolium-4-thiolate mesoion could be umpoled with sulfuryl chloride to yield a dicationic electrophile 3 that reacted with various electron-rich aromatic substrates to yield arylthio-substituted 1,3-dithiolium salts 13-25. Two of these compounds have been transformed to the corresponding symmetrical tetrathiafulvalenes 43 and 44, and their cyclovoltammetric behaviour recorded. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.