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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (04): 643-647. 上一篇    下一篇

研究简报

AlCl3催化对位取代苯胺与丙烯腈加成反应的研究

赵 莹*; 叶翠层; 谭晓燕; 杨 志   

  1. (中南林业科技大学应用化学研究所 株洲 412006)
  • 收稿日期:2008-03-21 修回日期:2008-08-20 发布日期:2009-04-20
  • 通讯作者: 赵 莹

Anilination of Acrylonitrile with p-Substituted Anilines Catalyzed by AlCl3

Zhao, Ying* ; Ye, Cuiceng; Tan, Xiaoyan; Yang, Zhi   

  1. (Institute of Applied Chemistry, Central South University of Forestry & Technology, Zhuzhou 412006)
  • Received:2008-03-21 Revised:2008-08-20 Published:2009-04-20
  • Contact: Zhao, Ying

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1723

被引次数

26

报道了无水AlCl3催化5种对位取代苯胺与丙烯腈发生Michael加成反应生成相应的N-氰乙基对位取代苯胺、N,N-二氰乙基对位取代苯胺, 结果表明, AlCl3对该类反应具有很高的催化活性. 在丙烯腈稍过量、较低温度、少量AlCl3催化剂的催化下, 主要生成N-氰乙基对位取代苯胺, 收率达88%～90%; 在丙烯腈过量较多、75～85 ℃及较多AlCl3催化剂的催化下, 主要生成 N,N-二氰乙基对位取代苯胺, 收率达88%～91%. 当加入Lewis碱NaOAc作助催化剂时有利于提高N-氰乙基对位取代苯胺的选择性和收率; 当加入Lewis 酸ZnCl2作助催化剂时则有利于提高N,N-二氰乙基对位取代苯胺的选择性和收率. 并对合成的5种N,N-二氰乙基对位取代苯胺用TG-DTA, UV, IR, NMR和元素分析进行了物性和结构表征.

关键词: AlCl3, N-氰乙基对位取代苯胺, N,N-二氰乙基对位取代苯胺

Michael addition reactions of acrylonitrile with p-substituted anilines have been carried out under various experimental conditions in the presence of AlCl3, AlCl3-NaOAc, or AlCl3-ZnCl2, resulting in N-β-cyanoethyl-p-substitutional anilines and N,N-bis(2-cyanoethyl)-p-substitutional anilines in high yields. And all of N,N-bis(2-cyanoethyl)-p-substituted anilines have been characterized by thermogravimetry, ultra-violet absorption spectrum, fourier transform infrared spectroscopy, electron paramagnetic resonance spec-tra, and elemental analyses.

Key words: N-β-cyanoethyl-p-substituted aniline, AlCl3, N,N-bis(2-cyanoethyl)-p-substituted aniline