In various solvents, 1,2-diiodotetrafluoroethane reacted with nitrogen containing nucleophiles, e.g. morpholine, readily to give tetrafluoroethylene and amide I under mild conditions. The reaction proceeds through a donor-acceptor complex, e.g. II, which has been isolated as a white solid and identified by elemental anal., 1H NMR, 19F NMR, MS and IR spectra. Thermolysis of II in different solvents was also studied. However, 2-chlorotetrafluoroethyl iodide did not react with amines, e.g. diethylamine or morpholine etc., to yield tetrafluoroethylene under similar conditions. Interestingly, ethylenediamine, which has a similar DN no. to diethylamine, did decompose 2-chlorotetrafluoroethyl iodide. These results indicated that the reaction was not only dependent on the nucleophilicity of the amines but also dependent on the steric effect of forming the complexes. In the presence of zinc or copper powder, 2-chlorotetrafluoroethyl iodide could also be decomposed by diethylamine and morpholine. A single electron transfer process has been proposed.

Key words: AMINES, DMF, DIETHYLENE GLYCOL P, ORGANONITROGEN COMPOUNDS, TETRAFLUORO ETHYLENE, ORGANO FLUORINE COMPOUNDS, NUCLEOPHILIC REACTION, ETHANE P, ACETONITRILE, IODOHYDROCARBON, FLUOROALKYLATION