Citation: Juan Li, Mingyue Cui, Rongqiang Tian, Zheng Duan, François Mathey. Cycloadditions of 1-iminylphosphirane complexes with allenes[J]. Chinese Chemical Letters, ;2021, 32(1): 449-452. doi: 10.1016/j.cclet.2020.05.026 shu

Cycloadditions of 1-iminylphosphirane complexes with allenes

College of Chemistry, Green Catalysis Center, International Phosphorus Laboratory, International Joint Research Laboratory for Functional Organophosphorus Materials of Henan Province, Zhengzhou University, Zhengzhou 450001, China

tianrq@zzu.edu.cn

duanzheng@zzu.edu.cn

Received Date: 25 April 2020
Revised Date: 6 May 2020
Accepted Date: 19 May 2020
Available Online: 28 May 2020

Figures(6)

A cascade carbonylative ring expansion and [2 + 2]/[4 + 2] cycloaddition of strained 1-iminylphosphirane complexes with aryl allenes were reported. The carbonylative ring expansion of 1-iminylphosphirane complexes provides an azaphosphacyclohexone complex intermediate with a C＝P double bond. The following [2 + 2] or dearomatic [4 + 2] cycloaddition of this intermediate with allenes is modulated by the aryl substituents on the imino carbon. The regioselective [2 + 2] cycloaddition with 1, 1-diarylallene provides an entry to bicyclo[4.2.0]octan-4-one skeletons featuring a four-membered phosphacyclobu-tane moiety. While dearomatic [4 + 2] cycloaddition was preferred with less aromatic naphthalene and yielded octahydrochrysene skeleton containing heteroatoms.
- Phosphirane,
- Allene,
- Ring expansion,
- Cycloaddition,
- Carbonylative,
- Heterocycle
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