REACTIONS INVOLVING FLUORIDE-ION .16. NUCLEOPHILIC-ATTACK ON A PERFLUOROTETRA-ALKYLETHYLENE AND A SYNTHESIS OF PERFLUOROTETRAMETHYLFURAN

Reaction of perfluoro-3,4-dimethylhex-3-ene (1) with oxygen nucleophiles gives products arising from attack on (1) as well as products arising from attack on the isomer, perfluoro-3,4-dimethylhex-2-ene (4). A novel cyclisation and defluorination is described for the reaction of (1) with MeOH and Et 3N, giving perfluorotetramethylfuran. Reactions of (1) with difunctional nucleophiles give cyclic products and oxidation of (1) with KMnO4 in acetone yields a diol. An unusual intramolecular nucleophilic displacement of fluoride from a perfluoroalkyl group is reported.