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

Abstract

Polyfluorinated tertiary amines were synthesized by the reactions of primary alkyl triflates (R FCH 2OSO 2CF 3, R F = CF 3, C 2F with the morpholide anion, preformed from perfluoro(5,6-dihydro-2 H-1,4-oxazine) on treatment with potassium fluoride (in tetraglyme). In the case of (CF 3) 2CHOSO 2CF 3, 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-2 H-1,4-oxazine) with polyfluoroalkylsiloxanes regardless of alkyl group variation.