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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (10): 1250-1253. 上一篇    下一篇

研究论文

三溴甲基芳烃合成新方法的研究

赵辉，陈红飙，刘展鹏，苏琼，林原斌*   

  1. (湘潭大学化学学院 湘潭 411105)
  • 收稿日期:2006-10-03 修回日期:2007-02-01 发布日期:2007-09-28
  • 通讯作者: 林原斌

Study on a New Method for Synthesis of Tribromomethylarenes

ZHAO Hui,CHEN Hong-Biao,LIU Zhan-Peng,SU Qiong,LIN Yuan-Bin*   

  1. (College of Chemistry, Xiangtan University, Xiangtan 411105)
  • Received:2006-10-03 Revised:2007-02-01 Published:2007-09-28
  • Contact: LIN Yuan-Bin

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1081

被引次数

7 | 1

报道了一种以三氯甲基芳烃与三溴化硼反应制备系列三溴甲基芳烃的新方法. 该方法反应条件温和, 收率高, 选择性好. 同时, 对影响该反应的因素进行了研究, 发现当芳环上连有强吸电子基团时, 不利于反应的进行, 而连有推电子基团时, 则有利于反应进行; 当取代基处于邻位时, 则明显阻碍反应的进行. 采用这种方法已合成了十多个三溴甲基芳烃, 其中1个是未见文献报道的新化合物.

关键词: 取代反应, 三溴甲基化, 三溴化硼, 三溴甲基芳烃, 三氯甲基芳烃

A novel method for synthesizing a series of tribromomethylarenes by halogen exchanging of tri-chloromethylarenes with boron tribromide was reported. Mild reaction conditions, high yield and good se-lectivity are most characteristic of this method. The influence factors and the mechanism of the reaction have also been studied. It was found that the reaction was accelerated obviously by the electron-donating substituting groups and decreased by the electron-withdrawing substituting groups and the reaction inhibited greatly when the groups were o-substituting groups. Thirteen compounds have been synthesized including a new compound with this method.

Key words: boron tribromide, trichloromethylarene, tribromomethylarene, displacement reaction, tribromomethylation