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化学学报
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化学学报 ›› 1987, Vol. 45 ›› Issue (4): 354-358. 上一篇    下一篇

研究论文

氟烷基化和氟烷氧基化的研究13: 2-卤四氟乙基物种的β-断裂

陈庆云;魏莫愁   

  1. 中国科学院上海有机化学研究所
  • 发布日期:1987-04-15

Studies on fluoroalkylation and fluoroalkoxylation 13: \b-fragementation of 2-halotetrafluoroethyl species

CHEN QINGYUN;WEI MOCHOU   

  • Published:1987-04-15

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651

被引次数

1

用典型自由基引发(hv,Cu,S2O4^2^-,ABN,DBP等),可以使2-卤四氟碘乙烷(1)(XCF2CF2I,X=Cl,I)产生四氟乙烯.从而证实了2-卤四氟乙基自由基在温和实验条件下能够发生β-断裂.1与亲核试剂(如PPh3,F^-,Cl^-,Br^-,CH3O^-,PhS^-等)作用结果,同样能得到四氟乙烯.这是符合离子型亲卤反应机理的.由此可见,1具有参与自由基机理和亲卤机理反应的双重性质.

关键词: 氯代烃, 烷基化, 化学键, 四氟乙烯, 氟代烃, 自由基反应, 亲核反应, 乙烷 P, 断裂机理, 碘代烃

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

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