Studies on fluoroalkylation and fluoroalkoxylation. Part 3. Perfluoroalkylation of olefins with perfluoroalkyl-iodides and copper in various solvenets

Perfluoroalkyl iodides react readily with simple olefins in the presence of catalytic amounts of copper in diglyme or acetic anhydride to give adducts in high yields. The reaction can be moderately accelerated by irradiation, partly suppressed with $\text{p}$-DNB and inhibited completely by hydroquinone. Fluorine-containing non-volatile amorphous solids were obtained when easily polymerized olefins, such as styrene and acrylates, were used as substrates. The reaction of perfluoroalkyl iodides and diallylic ether gave five-membered ring products under the same conditions. All the results seem to indicate that the reaction is a radical chain process induced by electron transfer. In DMSO, the main reaction may involve perfluoroalkylcopper intermediates which can be trapped by iodobenzene and hydroquinone and $\text{p}$-DNB show little inhibition effects.