22230-28-0Relevant academic research and scientific papers
A new synthesis of trifluoromethanethiolates - Characterization and properties of tetramethylammonium, cesium and di(benzo-15-crown-5)cesium trifluoromethanethiolates
Tyrra, Wieland,Naumann, Dieter,Hoge, Berthold,Yagupolskii, Yurii L.
, p. 101 - 107 (2003)
[NMe4]SCF3, CsSCF3 and [(B-15-C-5)2Cs]SCF3 (B-15-C-5: benzo-15-crown-5) are formed from reactions of the corresponding fluorides, trimethyl(trifluoromethyl)silane, Me3SiCF3, and elemental sulfur in glyme or THF. All compounds are colorless to pale ochre solids decomposing significantly above ambient temperature. Excellent agreement between experimental and theoretical vibrational frequencies, calculated at the B3PW91 level of theory, impressively confirms the salt-like nature of [NMe4]SCF3. The properties of the title compounds as nucleophilic SCF3 transfer reagents were checked with a variety of organic, organometallic and inorganic compounds.
Synthesis, structure and reactivity of a trifluoromethyl sulfide anionic salt stabilized with tetrakis(dimethylamino)ethylene dication (TDAE2+)
Kolomeitsev, Alexander,Medebielle, Maurice,Kirsch, Peer,Lork, Enno,Roeschenthaler, Gerd-Volker
, p. 2183 - 2185 (2000)
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.
Trifluoromethylthiolation of aromatic substrates using thiophosgene - fluoride salt reagents, and formation of byproducts with multi-carbon chains
Tavener, Stewart J.,Adams, Dave J.,Clark, James H.
, p. 171 - 176 (1999)
Reaction of potassium fluoride or tetramethylammonium fluoride with thiophosgene leads to the formation of a nucleophilic source of trifluoromethanethiolate, suitable for the preparation of trifluoromethyl aryl sulfides from activated haloaromatics. Analy
Preparation of trifluoromethyl aryl sulfides using silver(I) trifluoromethanethiolate and an inorganic iodide
Adams, Dave J.,Clark, James H.
, p. 1456 - 1460 (2000)
Reaction of silver(I) trifluoromethanethiolate (AgSCF3) with KI or tetra-n-butylammonium iodide in acetonitrile leads to the formation of a nucleophilic source of trifluoromethanethiolate. This source is capable of converting activated fluoro-, chloro-, bromo-, and iodoaromatics into the corresponding trifluoromethyl aryl sulfides under mild conditions. After successful reaction with tetra-n-butylammonium iodide, crystals of Bu4N[Ag3I4] precipitate from the reaction mixture. With less activated aromatic compounds, decomposition of the trifluoromethanethiolate anion occurs preferentially, giving bis(trifluoromethyl)disulfide, tetrakis(trifluoromethylthio)ethene, and 3,4,5,6- tetrakis(trifluoromethylthio)-1,2-dithiine. The use of copper(I) trifluoromethanethiolate and mercury(II) trifluoromethanethiolate for such reactions has also been investigated.
The preparation of trifluoromethyl aryl sulfides using KF and thiophosgene
Clark, James H.,Tavener, Stewart J.
, p. 169 - 172 (2007/10/03)
The trifluoromethanethiolate anion may be generated in situ by the reaction of thiophosgene with potassium fluoride in acetonitrile. This system is used to prepare trifluoromethyl aryl sulfides from activated fluoro- and chloroaromatic substrates via nucleophilic substitution.
