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.

Graphical abstractA new hypofluorite and vinyl ether.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► First example of an N-fluorocarbon hypofluorite was synthesized. ► New hypolfluorite was used to prepare the first N-fluorocarbon trifluorovinyl ether. ► Novel vinyl ether was successfully copolymerized with tetrafluoroethylene. ► Copolymer may have excellent potential for use in low temperature elastomers with further development.