University Chemistry ›› 2025, Vol. 40 ›› Issue (6): 160-166.doi: 10.12461/PKU.DXHX202408038

• Science Education • Previous Articles     Next Articles

Isolobal Analogy and Isovalent Relationships of 6-Electron Reagents in Electrophilic Alkene Cycloaddition Reactions

Zihao Guo, Shichen Ma, Kin Shing Chan   

  1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China
  • Received:2024-08-10 Accepted:2024-11-12 Published:2025-06-20
  • Contact: CHEN Jiancheng E-mail:kschan@nju.edu.cn

Abstract: This paper introduces a teaching approach for electrophilic alkene cycloaddition reactions, highlighting the use of isolobal analogy and isovalent relationships of 6-electron species as guiding principles. This method aims to help students comprehend the formation of key intermediates and products, such as bridged bromonium ions, epoxides, and aziridines, in common electrophilic cycloaddition processes.

Key words: Alkene epoxidation, Isolobal analogy, Carbene, Nitrene, Organic chemistry teaching