Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (8): 2277-2286.DOI: 10.6023/cjoc201903042 Previous Articles     Next Articles

Special Issue: 陈茹玉先生诞辰100周年

Articles

通过1-磷杂富烯合成含磷多环化合物

申宁宁, 刘艳杰, 田荣强, 段征, Francois Mathey   

  1. 郑州大学化学与分子工程学院 国际磷化学实验室 河南省有机磷功能分子国际联合实验室 郑州 450001
  • 收稿日期:2019-03-21 修回日期:2019-04-11 出版日期:2019-08-25 发布日期:2019-04-19
  • 通讯作者: 田荣强, 段征 E-mail:tianrq@zzu.edu.cn;duanzheng@zzu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21302174,21672193,21272218)、中国博士后科学基金(No.2017M622362)、郑州大学优秀青年发展基金(No.1621316006)资助项目.

Synthesis of Polycyclic Phosphacycles via 1-Phosphafulvene

Shen Ningning, Liu Yanjie, Tian Rongqiang, Duan Zheng, Mathey Francois   

  1. International Phosphorus Laboratory, International Joint Research Laboratory for Functional Organophosphorus Materials of Henan Province, College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001
  • Received:2019-03-21 Revised:2019-04-11 Online:2019-08-25 Published:2019-04-19
  • Contact: 10.6023/cjoc201903042 E-mail:tianrq@zzu.edu.cn;duanzheng@zzu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21302174, 21672193, 21272218), the China Postdoctoral Science Foundation (No. 2017M622362), and the Young Talent Research Fund of Zhengzhou University (No. 1621316006).

1-Phosphafulvenes are unique in their cycloaddition reactions, which act as 2π, 4π, and 6π systems and provide versatile and powerful approaches to various polycyclic systems. The reaction of 1-phosphafulvene with 1,4-benzoquinone and N-phenylmaleimide upon heating provided phosphapolycyclic rings in moderate to good yields. The possible mechanism included an oxidative addition of 1-phosphafulvene with 1,4-benzoquinone and successive Diels-Alder reactions with N-phenylmaleimide. The exocyclic C=C bond of 1-phosphafulvene is cruial to this reaction.

Key words: phosphafulvene, 1,4-benzoquinone, oxidative addition, cycloaddition