有机化学 ›› 2019, Vol. 39 ›› Issue (8): 2277-2286.DOI: 10.6023/cjoc201903042 上一篇    下一篇

所属专题: 元素有机化学合辑2018-2019 陈茹玉先生诞辰100周年

研究论文

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 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 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-磷杂富烯能够以2π、4π、6π体系参与环加成反应,并转化为多种磷杂多环化合物.报道了1-磷杂富烯和对苯醌以及N-苯基马来酰亚胺在加热条件下反应合成磷杂多环产物的新方法.研究结果表明对苯醌与1-磷杂富烯通过氧化加成反应产生一个易发生Diels-Alder反应的磷杂环戊烯中间体.该中间体与2分子N-苯基马来酰亚胺经过两次Diels-Alder反应形成磷杂多环化合物.研究还表明1-磷杂富烯环外双键对该反应的发生至关重要.

关键词: 磷杂富烯, 1,4-苯醌, 氧化加成, 环加成

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