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高等学校化学研究 ›› 2016, Vol. 32 ›› Issue (5): 775-780.doi: 10.1007/s40242-016-6158-7

• Articles • 上一篇    下一篇

Photolysis and Cycloaddition Reactivity of Diferrocenyl Substituted Cyclopentadienone

ZHANG Xiaoyong1,2, HAN Limin1, GAO Yuanyuan1, SHI Jiale1, SUO Quanling1   

  1. 1. Chemical Engineering College, Inner Mongolia University of Technology, Hohhot 010051, P. R. China;
    2. Department of Chemistry, Baotou Teacher's College, Baotou 014030, P. R. China
  • 收稿日期:2016-04-22 修回日期:2016-06-20 出版日期:2016-10-01 发布日期:2016-08-01
  • 通讯作者: SUO Quanling E-mail:szj010062@163.com
  • 基金资助:

    Supported by the National Natural Science Foundation of China(Nos.21266019, 21062011).

Photolysis and Cycloaddition Reactivity of Diferrocenyl Substituted Cyclopentadienone

ZHANG Xiaoyong1,2, HAN Limin1, GAO Yuanyuan1, SHI Jiale1, SUO Quanling1   

  1. 1. Chemical Engineering College, Inner Mongolia University of Technology, Hohhot 010051, P. R. China;
    2. Department of Chemistry, Baotou Teacher's College, Baotou 014030, P. R. China
  • Received:2016-04-22 Revised:2016-06-20 Online:2016-10-01 Published:2016-08-01
  • Contact: SUO Quanling E-mail:szj010062@163.com
  • Supported by:

    Supported by the National Natural Science Foundation of China(Nos.21266019, 21062011).

摘要:

The photolysis results of new diferrocenyl substituted cyclopentadienone(3) show that sunlight and air play an important role in the decomposition of compound 3, and two new compounds, 2-cyclopentenone(4) and α-pyrone(5), were obtained via photolysis of compound 3. The photolysis process was investigated by 1H NMR, and a plausible mechanism for the formation of compound 5 was deduced. The cycloaddition reactions of substituted cyclopentadienones(3, 7, 9) with maleimide gave substituted imides 8, 10, 11, 12 and an unprecedented diferrocenyl substituted 1H-pyrrol-3(2H)-one derivative 13, respectively. The structures of compounds 4, 5, 8, 10, 11, 12 and 13 were confirmed by X-ray single crystal diffraction analysis technique.

关键词: Cyclopentadienone, Reactivity, Photolysis, Cycloaddition, Crystal structure

Abstract:

The photolysis results of new diferrocenyl substituted cyclopentadienone(3) show that sunlight and air play an important role in the decomposition of compound 3, and two new compounds, 2-cyclopentenone(4) and α-pyrone(5), were obtained via photolysis of compound 3. The photolysis process was investigated by 1H NMR, and a plausible mechanism for the formation of compound 5 was deduced. The cycloaddition reactions of substituted cyclopentadienones(3, 7, 9) with maleimide gave substituted imides 8, 10, 11, 12 and an unprecedented diferrocenyl substituted 1H-pyrrol-3(2H)-one derivative 13, respectively. The structures of compounds 4, 5, 8, 10, 11, 12 and 13 were confirmed by X-ray single crystal diffraction analysis technique.

Key words: Cyclopentadienone, Reactivity, Photolysis, Cycloaddition, Crystal structure