Abstract
Fluoralkylamines (CF 3) 3−nN(CHF 2) n, n = 1 to 3, and analogous C 2F 5 derivatives exhibit a selective reactivity of the CHF 2 group towards Lewis acids like BCl 3, TiCl 4 and BBr 3, CHCl 2 and CHBr 2 groups being formed in nearly quantitative yield. Halogenated trialkylamines of the general formulae (CF 3) 3−nN(CHCl 2) n, n = 1 to 3, and (CF 3) 3−nN(CHBr 2) n, n = 1 and 2, were obtained for the first time and characterized by nmr, ir, Raman and mass spectra. The halogen exchange reaction proceeds via an intermediate immonium cation, but the chloro and bromoalkyl amines are non-ionic. Both (CF 3) 2NCHF 2 and (CF 3) 2NCHCl 2 undergo photochlorination to yield (CF 3) 2NCF 2Cl and (CF 3) 2NCCl 3.
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