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

Abstract

The first N-containing trifluorovinyl ether monomer (CF 3) 2NCF 2OCF CF 2 was synthesized. The starting perfluoroalkyl imine CF 3–N CF 2 was converted to the perfluoroalkyl amine (CF 3) 2NH by HF. The amine was converted into the carbamoyl fluoride (CF 3) 2NC(O)F via reaction with carbonyl fluoride COF 2 in the presence of NaF. The carbamoyl fluoride was subjected to catalytic fluorination with molecular F 2 in the presence of CsF to afford the hypofluorite (CF 3) 2NCF 2(OF). The hypofluorite was added to CFCl CFCl 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.