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化学学报
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化学学报 ›› 1988, Vol. 46 ›› Issue (1): 38-41. 上一篇    下一篇

研究论文

氟烷基化和氟烷氧基化的研究 21: 锌存在下全氟烷基碘与亚硝酸阴离子的反应及其机理探讨

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:1988-01-15

Studies on fluoroalkylation and fluoroalkoxylation 21: The single electron transfer (SET) reaction of perfluoroalkyl iodide with nitrite anion induced by zinc

CHEN QINGYUN;QIU ZAIMING   

  • Published:1988-01-15

PDF

527

被引次数

8

在过量锌粉的存在下, 全氟烷基碘(RFCF2I, RF:CF3CF2, Cl(CF2)n, n=3,5,7)(1)能与亚硝酸阴离子反应, 一步生成全氟烷基羧酸钠, 酸化后得到相应的羧酸. p-DNB不能阻止反应. NO3^-, SCN^-或F^-等阴离子在同样条件下和1反应只能生成1-氢-全氟烷烃.反应可能经锌单电子转移诱发的非链式自由基亲核取代机理.

关键词: 锌, 反应机理, 取代反应, 烷基化, 自由基反应, 有机氟化合物, 碘代烃, 酸根, 亚硝酸, 全氟代烃

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

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