Utilizing the typical radical initiating methods (hn, Cu, S2O42-, etc.), 2-halotetrafluoroethyl iodide (XCF2CF2I, X = Cl, I) (I) was converted into tetrafluoroethylene. It may be rationalized in terms of the b-fragmentation of 2-halotetrafluoroethyl radical. However, tetrafluoroethylene may also be obtained in the reaction of I with nucleophiles (PPh3, F-, Cl-, Br-, CH3O-, PhS-, etc.) through halophilic mechanism. Thus, it is shown that 2-halotetrafluoroethyl iodide has a dual reactivity undergoing both radical and halophilic reactions.

Key words: CHLOROHYDROCARBON, ALKYLATION, CHEMICAL BONDS, TETRAFLUORO ETHYLENE, FLUOROHYDROCARBON, FREE RADICAL REACTION, NUCLEOPHILIC REACTION, ETHANE P, FRACTURE MECHANISM, IODOHYDROCARBON