[p-((trifluorovinyl)oxy)phenyl]lithium: Formation, synthetic utility, and theoretical support for a versatile new reagent in fluoropolymer chemistry

The metal-halogen. exchange reaction of p-bromophenyl trifluorovinyl ether, p-BrC6H4OCF=CF2 (1), with tert-butyllithium in ether at -78 degrees C affords the title reagent, p-LiC6H4OCF=CF2 (2), in solution. Subsequent addition of appropriate silicon, phosphorus, or organic electrophiles yields a wide variety of new trifluorovinyl ether monomers for fluoropolymer chemistry. Ab initio calculations (MP2/6-31G*//6-31G* level) indicate that the (trifluorovinyl)oxy substituent stabilizes anion 2 by approximately 10 kcal/mol relative to the methoxy analogue.