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Citation: Jiaxi Xu, Ning Chen. Application of the Regioselective Rule in the Nucleophilic Ring Opening of Epoxides in Organic Chemistry Teaching[J]. University Chemistry, ;2020, 35(7): 166-170. doi: 10.3866/PKU.DXHX202001004 shu

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

Jiaxi Xu ,
Ning Chen

Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, P. R. China

Received Date: 2 January 2020

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.
- Epoxide,
- Regioselectivity,
- Nucleophilic ring opening,
- Teaching,
- Application,
- Rule
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