HALOGEN EXCHANGE OF FLUOROALKYL AMINES SYNTHESIS OF POLYCHLORO- AND BROMOTRIALKYLAMINES

Article abstract of DOI:10.1016/S0022-1139(00)84016-6

Fluoralkylamines (CF3)_3-nN(CHF2)n, n=1 to 3, and analogous C2F5 derivatives exhibit a selective reactivity of the CHF2 group towards Lewis acids like BCl3, TiCl4 and BBr3, CHCl2 and CHBr2 groups being formed in nearly quantitative yield.Halogenated trialkylamines of the general formulae (CF3)_3-nN(CHCl2)n, n=1 to 3, and (CF3)_3-nN(CHBr2)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 (CF3)2NCHF2 and (CF3)2NCHCl2 undergo photochlorination to yield (CF3)2NCF2Cl and (CF3)2NCCL3.