Synthesis of N,N-bis(trifluoromethyl)amino difluoromethylene trifluorovinyl ether

The first N-containing trifluorovinyl ether monomer (CF3)2NCF2OCFCF2 was synthesized. The starting perfluoroalkyl imine CF3–NCF2 was converted to the perfluoroalkyl amine (CF3)2NH by HF. The amine was converted into the carbamoyl fluoride (CF3)2NC(O)F via reaction with carbonyl fluoride COF2 in the presence of NaF. The carbamoyl fluoride was subjected to catalytic fluorination with molecular F2 in the presence of CsF to afford the hypofluorite (CF3)2NCF2(OF). The hypofluorite was added to CFClCFCl to provide a saturated halocarbon ether. Dechlorination of the ether with zinc in DMSO resulted in the title monomer. The new vinyl ether monomer readily copolymerizes with TFE.