Polyfluorinated systems resulting from free radical addition reactions

Abstract

The first part of this work was to synthesise partially fluorinated reactive compounds and then to study their reactivity towards nucleophiles and electrophiles. These reactive compounds were obtained in a two step process from both cyclopentane and adamantane and in a three step process for cyclopentanol. The first step was the free radical addition of the cycloalkanes, cycloalcohol to hexafluoropropene via thermal and/or radiochemical alkylations. For the cyclic alkane derivatives, the second step was a stereospecific dehydrofluorination of the fluorocarbon chain, whereas for the cyclic alcohol, a dehydration and then dehydrofluorination were performed to give the conjugated diene. Finally, the fluoroalkene reactivity was studied via nucleophilic and electrophilic addition reactions. The second part of my work was to study the free radical addition of tertiary amines to hexafluoropropene, an example is illustrated below.