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.