[P-((TRIFLUOROVINYL)OXY)PHENYL]LITHIUM - FORMATION, SYNTHETIC UTILITY, AND THEORETICAL SUPPORT FOR A VERSATILE NEW REAGENT IN FLUOROPOLYMERCHEMISTRY

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