Polyfluoroalkylation and polyfluoroalkoxylation of perfluoro-(5,6-dihydro-2H-1,4-oxazine) in the presence of fluoride anion

Polyfluorinated tertiary amines were synthesized by the reactions of primary alkyl triflates (RFCH2OSO2CF3, R-F = CF3, C2F5, CHF2) with the morpholide anion, preformed from perfluoro(5,6-dihydro-2H-1,4-oxazine) on treatment with potassium fluoride (in tetraglyme). In the case of (CF3)(2)CHOSO2CF3, polyfluoroalkoxylated oxazine was obtained by replacement of the imidoyl fluorine. A similar imidoyl fluorine substitution reaction occurred in the treatment of perfluoro(5,6-dihydro-2H-1,4-oxazine) with polyfluoroalkylsiloxanes regardless of alkyl group variation. (C) 1998 Elsevier Science S.A. All rights reserved.