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

Electrochemical fluorination (ECF) of various heterocyclic compounds h as been investigated. Alpha,omega-Dimorpholinoalkanes of different cha in length (n = 1-6) and of morpholinocyclohexene gave the perfluoro de rivatives in yields up to 45 %. The crystal and molecular structures o f the perfluorinated compounds are presented. The mechanism of ECF for these compounds is discussed on the basis of a steric model. Perfluor ocarbon emulsions of second generation were prepared by means of F-dim orpholines 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 ch emically inert and non-toxic. They are useful for blood substitutes in two ways: as co-surfactants to stabilize emulsions with perfluorocarb ons and as oxygen carriers instead of perfluorocarbons. The high densi ty 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 ar e ideal solubilizers for perfluorocarbons with hydrocarbons and vice v ersa. The diethers with short hydrocarbon spacer and long R(F)-tail ca n be applied in biological systems, because they are not soluble in li pid 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-genop erfluoroalkanes) are characterized and discussed. 1H-perfluoroalkane i s also formed by nucleophilic attack on perfluoroalkyl halide.