Trifluoromethanethiolate ion. Part 3. Reactions with tetrafluoropyridazine and tetrafluoropyrimidine

Abstract
Reactions of tetrafluoropyridazine (1) with gaseous thiocarbonyl difluoride or its liquid trimer, viz. bis(trifluoromethyl) trithiocarbonate, in the presence of caesium fluoride yield, selectively, 3,4,6-trifluoro-5-trifluoromethylthiopyridazine (2) or 3,6-difluoro-4,5-bis(trifluoromethylthio)pyridazine (3) depending on the reactant ratio; with an excess of the CF3S ion source a small amount of 3-fluoro-4,5,6-tris(trifluoromethylthio)pyridazine (4) was formed. The reactions of tetrafluoropyrimidine (5) proceeded unselectively to give mixtures of 2,4,5-trifluoro-6-trifluoromethylthiopyrimidine (6), 2,4-difluoro-5,6-bis(trifluoromethylthio)pyrimidine (7), 2,5-difluoro-4,6-bis(trifluoromethylthio)pyrimidine (8), and in some cases 5-fluoro-2,4,6-tris(trifluoromethylthio)pyrimidine (9). The new trifluoromethylthio derivatives of pyridazine and pyrimidine have been characterized by b.p., 19F n.m.r., and m.s. data.