Synthesis, structure and reactivity of a trifluoromethyl sulfide anionic salt stabilized with tetrakis(dimethylamino)ethylene dication (TDAE(2+))

A synthesis of the stable ionic trifluoromethanethiolate salts, TDAE(2+)2SC F(3)(-) (1) and TDAE(2+)SCF(3)(-)Cl(-) (2) was accomplished in quantitative yields via reduction of bis(trifluoromethyl) disulfide and trifluoromethan esulfenyl chloride using tetrakis(dimethylamino) ethylene (TDAE). The salts were found to be stable up to their melting points. The trifluoromethaneth iolate salt [TDAE(2+)2SCF(3)(-) (1)] was for the first time characterized b y X-ray structural analysis (orthorhombic, Pbca, a=1434.0(1), b=1178.1(1), c= 2203.2(1) pm) and cyclic voltammetry. Several reactions show the synthet ic utility of this new reagent.