PERFLUOROALKYLATION OF 2-MERCAPTOBENZOTHIAZOLE AND ITS ANALOGUES WITH PERFLUOROALKYL IODIDES BY AN SRN1 REACTION

Article abstract of DOI:10.1016/S0022-1139(00)80303-6

The thiolates, generated in situ by the reaction of 2-mercaptobenzothiazole (1) and its analogues (2) and (3) with sodium hydride, react under UV irradiation with perfluoroalkyl iodides (4)-(8) to give the corresponding heteroaromatic perfluoroalkyl sulfides (9)-(18) in 50-98percent yields.The fact that the UV irradiation increases the conversion of perfluoroalkyl iodides and that the radical scavenger di-tert-butylnitroxide suppresses the reaction demonstrates that the reaction proceeds via an S_RN1 mechanism.