Heterocyclic polyfluoro-compounds. Part 30. Perfluoroalkylation of trifluoro-1,2,4-triazine

Abstract

Reaction of trifluoro-1,2,4-triazine with hexafluoropropene and caesium fluoride in the absence of solvent leads to successive replacement of fluorine by perfluoroisopropyl groups to give 5-mano-, 3,5- and possibly 3,6-di-, and tri-substituted derivatives. Similarly, perfluoro-2-azapropene yields 5- and some 6-, 3,6-bis-, and tris-perfluorodimethylamino-derivatives.

Pyrolysis of trifluoro-1,2,4-triazine at 500 °C/42 h yields trifluoro-1,3,5-triazine (32%); of perfluoro(tri-isopropyl-1,2,4-triazine) at 560 °C/0.26 s yields perfluoroisobutyronitrile and perfluoro-2,5-dimethylhex-3-yne; and of perfluoro(trisdimethylamino-1,2,4-triazine) at 620 °C/2.4 s yields N,N-bis(trifluoromethyl)cyanamide and perfluorobis(dimathylamino)acetylene.