S(RN)1 REACTIONS OF 2,2,2-TRIFLUOROETHYL HALIDES WITH THIOLATE IONS

2,2,2-Trifluoroethyl chloride, bromide, iodide but not fluoride react with thiolate ions in DMF under laboratory illumination at 30-50 degre es C to give the 2,2,2-trifluoroethylthiol derivatives in high yields. The acceleration by UV irradiation, suppression by p-dinitrobenzene o r hydroquinone and detection of trifluoroethyl radical by ESR spectros copy show that the reactions occur by S(RN)1 mechanism. The initiation step may be spontaneous or thermal electron transfer between thiolate and halides because the reactions can occur in dark. (C) 1998 Elsevie r Science S.A. All rights reserved.