Chinese Journal of Organic Chemistry >
Synthesis of Polycyclic Phosphacycles via 1-Phosphafulvene
Received date: 2019-03-21
Revised date: 2019-04-11
Online published: 2019-04-19
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
Shen Ningning , Liu Yanjie , Tian Rongqiang , Duan Zheng , Mathey Francois . Synthesis of Polycyclic Phosphacycles via 1-Phosphafulvene[J]. Chinese Journal of Organic Chemistry, 2019 , 39(8) : 2277 -2286 . DOI: 10.6023/cjoc201903042
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