Sodium dithionite initiated reactions of 1-bromo-1-chloro-2,2,2-trifluoroethane with enol ethers of cyclic ketones

Sodium dithionite initiated addition of 1-bromo-1-chloro-2,2,2-trifluoroethane to β-pinene

“…In most of the published works, including our earlier studies of the reactions of CF 3 CHClBr with enol ethers [6,7], equimolar amounts of the initiator and a perhaloalkane were reported to be necessary to achieve good yields. However, in the present case, as little as 0.25 equivalent of Na 2 S 2 O 4 was found to be satisfactory.…”

“…In the preceding papers [6][7][8], we reported that sulfinatodehalogenation procedure could be applied to 1-bromo-1-chloro-2,2,2-trifluoroethane, commercially available as Halothane 1 (inhalation anaesthetic), to generate CF 3 CHCl . radicals which readily reacted with vinyl ethers [6,7] and with pyrroles [8].…”

Selective fluoroalkylation of thiophenols by 1,2-dibromotetrafluoroethane activated by sulfur dioxide

“…Introduction of halocarbon fragments, containing other halogen atoms besides fluorine, into different organic substrates allows the synthesis of new polyfluoroalkyl substrates as well as transformation of fluorine containing substituents to more complex groups [1][2][3][4][5][6][7][8][9][10][11][12][13][14].…”

Sodium dithionite initiated fluoroalkylation of trimethoxybenzenes, mesitylene and pyrroles with BrCF2CF2Br

“…water-free dimethylsulphoxide, temperature of 75 8C and prolonged reaction time, perfluoroalkylation of N, S and O heteroaromatics and activated benzenes with long chain perfluoroalkyl chlorides has also been reported [8]. In our laboratory, it has been found that the Na 2 S 2 O 4 /acetonitrile/H 2 O system is also able to promote addition of polyhaloalkanes, i.e.1-bromo-1-chloro-2,2,2-trifluoroethane (Halothane 1 ) [9][10][11][12] and dibromodifluoromethane [13,14] to various electron-rich unsaturated compounds but most attempts to alkylate aromatic and heteroaromatic compounds with these reagents were unsuccessful. The only successful exceptions were reactions of 1-bromo-1-chloro-2,2,2-trifluoroethane with 1,3,5-trimethoxybenzene and with pyrroles, which resulted in coupling of one molecule of CF 3 CHClBr with two molecules of the aromatic compound to give, respectively, trifluoromethyl-bis(2,4,6-trimethoxyphenyl)methane [15] and 5-(trifluoromethyl)-dipyrromethanes [16] in a 38-50% yields.…”