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紫外辐照法合成环蕃醛

金振康,刘和文()   

  1. 中国科学技术大学化学与材料科学学院 合肥 230026
  • 收稿日期:2019-05-20 出版日期:2019-12-01
  • 通讯作者: 刘和文
  • 基金资助:
    国家自然科学基金(51673181)项目资助

Synthesis of Cyclophanealdehyde by Ultraviolet Irradiation

JIN Zhenkang,LIU Hewen()   

  1. School of Chemistry and Materials Science,University of Science and Technology of China,Hefei 230026,China
  • Received:2019-05-20 Published:2019-12-01
  • Contact: LIU Hewen
  • Supported by:
    Supported by the National Natural Science Foundation of China(No.51673181)

摘要：

利用254 nm紫外光对[2.2]对环蕃氯仿溶液进行辐照,得到两种主要产物4-醛基-[2.2]-对环蕃和4,4'-(乙基-1,2-二取代)二苯甲醛,利用核磁共振波谱仪(NMR)和气相色谱-质谱联用(GC-MS)技术手段对产物的结构进行分析研究。 同时对反应条件进行探究,发现当氯仿和水同时存在时才能生成醛基,并由此提出了提出了可能的反应机理:通过瑞默-提曼反应使CHCl2·自由基加成到苯环上并进一步生成醛基。

关键词: 环蕃, 环蕃醛, 紫外辐照

Abstract:

In this paper, the chloroform solution of [2.2]paracyclophane is irradiated under 254 nm ultraviolet light to yield two main products, i.e. 4-formyl[2.2]paracyclophane and 4,4'-(ethane-1,2-diyl)dibenzaldehyde. The structures of the products are characterized by nuclear magnetic resonance spectroscopy (NMR), gas chromatography-mass spectrometer (GC-MS). The reaction conditions are explored. The coexistence of chloroform and water is important to form the aldehyde products and a possible reaction mechanism that the CHCl2· radical is added to the benzene ring and further forms an aldehyde group by Reimer-Tiemann reaction is proposed.

Key words: cyclophane, cyclophanealdehyde, ultraviolet irradiation

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