LIQUID-PHASE PHOTOFLUORINATION WITH ELEMENTAL FLUORINE .2. SYNTHESIS OF PERFLUOROTERTIARY AMINES

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.