Zinc can induce the reaction of RI (R = Cl(CF2)4, Cl(CF2)6, Cl(CF2)8] with pyrrole readily to give the regioselective products, 2-perfluoroalkylpyrrole in DMSO or DMF. However, in dioxane the homo-couple product R2 is the main product. This reaction can be suppressed by p-dinitrobenzene and afford the five-membered ring compounds in the presence of diallyl ether. All these results indicate that the radical mechanism induced by the single electron transfer from zinc may be involved. The solvent effects are also discussed.

Key words: INITIATOR, ZINC, ALKYLATION, ORGANO FLUORINE COMPOUNDS, PYRROLE P, IODOHYDROCARBON, PERFLUORO-HYDROCARBON, SINGLE ELECTRON TRANSFER REACTION