Abstract
The acid RfCH2CO2H (1)[Rf= CF3(C2F5)2C] derived from the tetrafluoroethylene pentamer (2) by base hydrolysis has been converted by Kolbe electrolysis into the dimer RfCH2CH2Rf(3). The salt RfCH2CO2Ag (4) with bromine afforded RfCH2Br (5) which was unreactive to nucleophiles under a variety of conditions. RfCH2COCl (6) with sodium azide under Curtius reaction conditions gave (RfCH2NH)2CO (7), whereas reaction of (6) with trimethylsilyl azide or sodium azide–18-crown-6 gave RfCH2NCO (8). RfCH2NCO and cyclohexylamine gave RfCH2NHCONHC6H11(9). Neither urea, (7) or (9), could be hydrolysed. RfCH2COCl (6) reacted with ammonia to give RfCH2CONH2(10) and with cyclohexylamine to yield RfCH2CONHC6H11(11). The amide (10) under Hofmann degradation conditions gave the urea (7). The acid (1) reacted with sodium azide in 25% oleum to yield RfCH2NH3+ HSO4–(12) which, on reaction with dilute base, gave RfCH2NH2(13). Reaction of RfCH2NH3(13) or RfCH2NH3+ HSO4–(12) with sodium nitrite afforded RfCHN2(14) as a stable liquid.
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