T. Ono et al., LIQUID-PHASE PHOTOFLUORINATION WITH ELEMENTAL FLUORINE .2. SYNTHESIS OF PERFLUOROTERTIARY AMINES, Journal of fluorine chemistry, 73(2), 1995, pp. 267-272
The tertiary amines derived from hexafluoropropene dimers were subject
ed to liquid-phase photofluorination (LPPF). The corresponding perfluo
rotertiary amines, which were difficult to synthesize by the conventio
nal fluorination methods such as electrochemical fluorination and indi
rect fluorination using high-valency metal fluorides, were obtained in
good yields. Prepared by this method were F-(N,N-dimethyl-2-methylpen
tyl)amine 3, F-(N,N-diethyl-2-methylpentyl)amine 4, F-3-(1-pyrrolidino
)-2-methylpentane 11, F-(N,N-dimethyl-1,1-dimethylbutyl)amine 13. Disc
ussion on the regioselectivity in the reaction of F-2-methyl-2-pentene
(D-II) with secondary amines is also included in connection with the
necessity of preparing a regioselective adduct, 3-(1-pyrrolidino)-F-2-
methyl-2-pentene, for the synthesis of 11.