2,2,2-Trifluoroethyl aryl selenides: ArSeCH2CF3 (Ar = C6H5, p-CH3C6H4) and their derivatives ArSe(O)CH2CF3 and ArSe(X)2CH2CF3 (X = Cl, Br, OOCCF3)

Article abstract of DOI:10.1016/0022-1139(93)02933-6

The title selenides were prepared in good yield by reacting the appropriate aryl selenolate anions with 2,2,2-trifluoroethyltosylate in refluxing tetrahydrofuran.These unsymmetrical bivalent selenides can be oxidised to the corresponding compounds of tetravalent selenium, ArSe(X)2CH2CF3 (X=Cl and Br) with elemental chlorine and bromine.The latter, upon basic hydrolysis, gave the selenoxides, ArSe(O)CH2CF3.Selenoxides have also been formed by direct reaction of the selenides with hydrogen peroxide.Upon reaction with trifluoroacetic anhydride, these gave trifluoroacetate derivatives, ArSe(OOCCF3)2CH2CF3, in quantitative yield.The compounds have been characterized via elemental analysis, infrared spectra, 1H and 19F NMR spectra, and mass spectra.