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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (12): 1904-1910. 上一篇    下一篇

研究论文

酮腙与一氧化氮的偶氮-硝化反应

杨得锁*,1,2，郭亚宁1，朱海云1，吴隆民2   

  1. (1宝鸡文理学院化学化工系 宝鸡 721013)
    (2兰州大学功能有机分子化学国家重点实验室 兰州 73000)
  • 收稿日期:2010-04-01 修回日期:2010-07-23 发布日期:2010-09-17
  • 通讯作者: 杨得锁 E-mail:yangds09@163.com

Azotization and Nitration Reaction of Ketone Arylhydrazones with Ni-tric Oxide

Yang Desuo*,1,2 Guo Yaning1 Zhu Hai-yun1 Wu Longmin2   

  1. (1 Department of Chemistry & Engineering, Baoji University of Arts & Science, Baoji 721013)
    (2 State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000)
  • Received:2010-04-01 Revised:2010-07-23 Published:2010-09-17

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在微量O2存在时, 酮腙与NO发生偶氮-硝化反应, 高选择性地生成了a-硝基偶氮化合物. 产物结构经NMR, IR, MS, HR-ESI-MS和X射线单晶衍射等技术确证. 通过高效液相色谱对反应体系中不同O2含量(空气)下的产物组成进行分析, 结果表明体系中O2含量的控制对a-硝基偶氮化合物的生成反应的选择性有较大影响.

关键词: 酮腙, 一氧化氮, α-硝基偶氮化合物

Ketone arylhydrazones reacted with nitric oxide in the presence of microquantitative amount of oxygen to give a-nitro azo-compounds in high selectively. The reaction occurred most likely by a tandem nitra-tion-azotization reaction. Structures of the products were characterized by NMR, IR, MS, HR-ESI-MS, and X-ray crystallography. By analyzing the composition of products using HPLC under oxygen concentration in system, the results showed that controlling oxygen content in the reaction system has a greater influence on the reaction selectivity of producing α-nitro azo-compounds.

Key words: ketone arylhydrazone, nitric oxide, α-nitro azo-compound