有机化学 ›› 1987, Vol. 7 ›› Issue (5): 364-369. 上一篇    下一篇

研究论文

氟烷基化和氟烷氧基化的研究18.2-卤四氟碘乙烷与含氮亲核试剂的反应

陈庆云;裘再明   

  1. 中国科学院上海有机化学研究所
  • 发布日期:1987-10-25

Studies on fluoroalkylation and fluoroalkoxylation 18. reactions of 2-halotetrafluoroethyl iodide with nitrogen containing nucleophiles

CHEN QINGYUN;QIU ZAIMING   

  • Published:1987-10-25

关键词: 胺, DMF, 二乙二醇醚 P, 有机氮化合物, 四氟乙烯, 有机氟化合物, 亲核反应, 乙烷 P, 乙腈, 碘代烃, 氟烷基化, 烷氧化反应

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

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