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化学学报
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化学学报 ›› 1988, Vol. 46 ›› Issue (3): 258-263. 上一篇    下一篇

研究论文

氟烷基化和氟烷氧基化的研究 23: 锌单电子转移引发全氟烷基碘与吡咯的反应

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:1988-03-15

Studies on fluoroalkylation and fluoroalkoxylation 23: The single electron transfer induced reaction of perfluoroalkyl iodides with pyrrole by zinc

CHEN QINGYUN;QIU ZAIMING   

  • Published:1988-03-15

PDF

586

被引次数

7

在二甲亚砜或二甲基甲酰胺中, 锌能迅速引发全氟烷基碘(1)与吡咯的反应, 生成2-氟烷基吡咯(3); 在二氧六环中, 主要生成全氟烷基碘的偶合产物5; 在乙腈、二乙二醇二甲醚或苯等溶剂中, 则同时生成3和5, 反应能被二硝基苯阻止. 加入二烯丙基醚能得到氟烷基取代的四氢呋喃衍生物. 反应可能经锌单电子转移引发的自由基机理. 对溶剂效应作了讨论.

关键词: 引发剂, 锌, 烷基化, 有机氟化合物, 吡咯 P, 碘代烃, 全氟代烃, 单电子转移反应, 烷氧化反应

Zinc can induce the reaction of RI (R = Cl(CF2)4, Cl(CF2)6, Cl(CF2)8] with pyrrole readily to give the regioselective products, 2-perfluoroalkylpyrrole in DMSO or DMF. However, in dioxane the homo-couple product R2 is the main product. This reaction can be suppressed by p-dinitrobenzene and afford the five-membered ring compounds in the presence of diallyl ether. All these results indicate that the radical mechanism induced by the single electron transfer from zinc may be involved. The solvent effects are also discussed.

Key words: INITIATOR, ZINC, ALKYLATION, ORGANO FLUORINE COMPOUNDS, PYRROLE P, IODOHYDROCARBON, PERFLUORO-HYDROCARBON, SINGLE ELECTRON TRANSFER REACTION

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