PERFLUORINATED AND PARTIALLY FLUORINATED ORGANIC-COMPOUNDS - PREPARATION, CHARACTERIZATION AND APPLICATION

Electrochemical fluorination (ECF) of various heterocyclic compounds has been investigated. Alpha,omega-Dimorpholinoalkanes of different chain length (n = 1-6) and of morpholinocyclohexene gave the perfluoro derivatives in yields up to 45 %. The crystal and molecular structures of the perfluorinated compounds are presented. The mechanism of ECF for these compounds is discussed on the basis of a steric model. Perfluorocarbon emulsions of second generation were prepared by means of F-dimorpholines and F-cyclohexylmorpholine, acting both as oxygen carriers and as interfacial active compounds (IFACs). The stabilizing effect of these IFACs is interpreted. Semifluorinated alkanes, R(F)R(H), are chemically inert and non-toxic. They are useful for blood substitutes in two ways: as co-surfactants to stabilize emulsions with perfluorocarbons and as oxygen carriers instead of perfluorocarbons. The high density of perfluorocarbons cause problems in some field of application in medicine. Therefore symmetrical diethers of the type R(F)(CH2)(m)O(CH2)(n)O(CH2)(m)R(F) were synthesized. These are inert and biocompatible compounds. Diethers with long R(F)-tail and long hydrocarbon spacer are ideal solubilizers for perfluorocarbons with hydrocarbons and vice versa. The diethers with short hydrocarbon spacer and long R(F)-tail can be applied in biological systems, because they are not soluble in lipid tissues. Perfluorocarbons (e. g. F-decalin, F-octane) are used as medical tools in ophthalmology, their purity is essential. Not totally fluorinated compounds (1H-perfluoroalkanes, alpha,omega-dihydro-genoperfluoroalkanes) are characterized and discussed. 1H-perfluoroalkane is also formed by nucleophilic attack on perfluoroalkyl halide.