University Chemistry ›› 2020, Vol. 35 ›› Issue (7): 166-170.doi: 10.3866/PKU.DXHX202001004

Special Issue:

• Between Teacher and Student • Previous Articles     Next Articles

Application of the Regioselective Rule in the Nucleophilic Ring Opening of Epoxides in Organic Chemistry Teaching

Jiaxi Xu(), Ning Chen   

  • Received:2020-01-02 Accepted:2020-02-06 Published:2020-03-02
  • Contact: Jiaxi Xu


The regioselective rule in the nucleophilic ring opening reactions of unsymmetric epoxides is a general selective rule of typical aliphatic three-membered heterocycles. The regioselectivity controlling factors were discussed from the stability viewpoint of transition states in the nucleophilic ring opening reactions of unsymmetric epoxides. The applications of the regioselective rule in teaching the regioselectivities of electrophilic additions of olefins involving three-membered heterocyclic intermediates in their reaction mechanisms were introduced. The students can gain a thorough understanding of mechanisms and selectivities in different reactions and improve teaching efficiency and results.

Key words: Epoxide, Regioselectivity, Nucleophilic ring opening, Teaching, Application, Rule