University Chemistry ›› 2022, Vol. 37 ›› Issue (12): 2112089.doi: 10.3866/PKU.DXHX202112089

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Revealing the Stereoselective Rule of Electrocyclic Reactions of Chain Conjugated Polyenes by Performing Quantum Chemical Calculations

Xuexiang Ma, Chengbu Liu, Dongju Zhang()   

  • Received:2021-12-30 Accepted:2022-02-08 Published:2022-03-14
  • Contact: Dongju Zhang


The electrocyclization reaction of chain conjugated polyenes is an important teaching content in the basic chemistry course of undergraduates. Taking the simplest 4n and (4n+2) chain conjugated polyenes as examples, this paper designs a teaching case based on quantum chemical calculations to quantitatively and intuitively describe the stereoselectivity of electrocyclization reactions of chain conjugated polyenes, in order to enable students to deepen their understanding of the electrocyclization reaction mechanism, frontier orbital theory, and molecular orbital symmetry conservation principle.

Key words: Chain conjugated polyenes, Electrocyclic reactions, Stereoselectivity, DFT calculations