Perfluoroalkylation of aromatic systems

Abstract

I. We have concentrated on the synthesis of aromatic systems containing CH(_2)R(_F) groups, where R(_F) is a bulky group derived from hexafluoropropene dimer, using fluoride ion induced methodology. A variety of procedures have been explored and methods of synthesis are described. We have made a major advance in this area by the simple expedient of extracting the polyfluoroalkylated products directly into commercially available perfluorinated fluids: FC-84 (bp 8O C), enabling simple purification. II. This new class of perfluoroalkylated derivatives has allowed us to explore some further chemistry. Synthesis and reactions are presented and the results are discussed in terms of electronic effects of the perfluoroalkyl group on the benzene ring. The unusual miscibility properties of fluorocarbon solvents have also prompted us to investigate the potential utility of these systems for dyes and catalysis. III. Synthetically useful perfluoroalkylated-s-triazines have been synthesised from 2,4,6-trifluoro-s-triazine, by fluoride ion induced reaction with hexafluoropropene. These systems so produced were extensively studied, and particular attention was paid to reactions with oxygen-centered nucleophiles. Model chemistry to demonstrate that attachment of perfluorocarbon groups to surfaces could be a useful form of treatment by using this methodology and was explored.