University Chemistry ›› 2023, Vol. 38 ›› Issue (4): 237-242.doi: 10.3866/PKU.DXHX202210017

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A Cleavage-Recombination Strategy of P—C(sp2) Bond to Assemble New Organic Phosphine

Qilin Wang1,*(), Minghao Wang2, Jixiang Xu2, Junhua Liu2   

  1. 1 College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, Henan Province, China
    2 School of Information Engineering, Henan Kaifeng College of Science Technology and Communication, Kaifeng 475004, Henan Province, China
  • Received:2022-10-10 Accepted:2022-12-11 Published:2023-03-01
  • Contact: Qilin Wang


In this experiment, we introduce the organic phosphine frontier to organic laboratory teaching. Starting from easily accessible and cost-effective triphenylphosphine and ethyl propionate, this experiment proceeds successfully under mild conditions to accomplish the highly efficient synthesis of new organic phosphine. It has the advantages of short reaction time and simple operation. The structure of the product was determined by melting point measurements, nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. Through this experiment, students can understand the frontier field of phosphine chemistry, deepen the understanding of the whole process of reaction, and further master the separation and analysis methods commonly used in the laboratory. This experiment is conducive to training students to comprehensively use the knowledge of organic chemistry, analytical chemistry and instrumental analysis to analyze and solve problems. It can also stimulate students' interest in scientific research and contribute to the cultivation of innovative talents.

Key words: Organic phosphine, Cleavage-recombination, Rearrangement, Laboratory teaching