Synthesis, structure and reactivity of a trifluoromethyl sulfide anionic salt stabilized with tetrakis(dimethylamino)ethylene dication (TDAE2+)

Abstract

A synthesis of the stable ionic trifluoromethanethiolate salts, TDAE²⁺2SCF₃⁻ (1) and TDAE²⁺SCF₃⁻Cl⁻ (2) was accomplished in quantitative yields via reduction of bis(trifluoromethyl) disulfide and trifluoromethanesulfenyl chloride using tetrakis(dimethylamino) ethylene (TDAE). The salts were found to be stable up to their melting points. The trifluoromethanethiolate salt [TDAE²⁺2SCF₃⁻ (1)] was for the first time characterized by 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 synthetic utility of this new reagent.