In the presence of excess amts. of zinc powder, perfluoroalkyl iodides react with sodium nitrite in aprotic solvents to give the corresponding perfluoroalkanoic acids. The reaction can not be inhibited by 4-O2NC6H4NO2. Other anions, e.g. NO3-, SCN-, and F-, fail to couple with fluoroalkyl radical and give only 1-H-perfluoroalkane. A non-chain radical anion mechanism induced by single electron transfer from zinc is proposed.

Key words: ZINC, REACTION MECHANISM, SUBSTITUTION REACTION, ALKYLATION, FREE RADICAL REACTION, ORGANO FLUORINE COMPOUNDS, IODOHYDROCARBON, ACID RADICAL, NITROUS ACID, PERFLUORO-HYDROCARBON