Reactions of bromotrifluoromethane and related halides: synthesis of trifluoromethyl sulphides from disulphides

New Dimensions in Rongalite Chemistry: The Land of Opportunities in Organic Synthesis and Material Sciences

“…has synthesized aromatic as well as aliphatic fluorinated sulphides 71 from easily available bromotrifluoromethane and disulphides 70 using rongalite in the presence of aq. DMF (Scheme ) . On the contrary, in 1992, the same research group has also reported perfluoroalkylsulfides 73 from disulphides 72 using rongalite (Scheme ) …”

Selective oxidation and chlorination of trifluoromethylsulfide using trichloroisocyanuric acid in ionic liquid

“…Thereinto, the reaction of aryl disulfide with trifluoromethyl bromide in the presence of sulfoxylate anion radical precursors developed by Wakselman et al [23,24] constitute an important method of synthesis. It is widely used in experiment and industry during a long time.…”

“…There are many methods about the synthesis of aryltrifluoromethylsulfides [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33]. Thereinto, the reaction of aryl disulfide with trifluoromethyl bromide in the presence of sulfoxylate anion radical precursors developed by Wakselman et al [23,24] constitute an important method of synthesis.…”

Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation

“…The economy of this method, as distinct from previous methods [196,241–248], lies in the fact that the thiolate released by the first nucleophilic attack on the disulfide reacts directly with a second equivalent of perfluoroalkyliodide, to form a second equivalent of the desired perfluoroalkyl sulfide (Scheme 65). This approach thus combines two principles of trifluoromethylation, i.e., nucleophilic attack of the R F -anion on the disulfide and reaction of a radical anion with a thiol as noted in section 4.1.…”