The metal−halogen exchange reaction of p-bromophenyl trifluorovinyl ether,
p-BrC6H4OCFCF2
(1), with tert-butyllithium in ether at −78
°C affords the
title reagent,
p-LiC6H4OCFCF2
(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.
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