大学化学 >> 2020, Vol. 35 >> Issue (7): 166-170.doi: 10.3866/PKU.DXHX202001004

所属专题: 有机化学课程与实验教学

师生笔谈 上一篇    下一篇

环氧乙烷亲核开环的区域选择性规则在有机化学教学中的应用

许家喜(), 陈宁   

  • 收稿日期:2020-01-02 录用日期:2020-02-06 发布日期:2020-03-02
  • 通讯作者: 许家喜 E-mail:jxxu@mail.buct.edu.cn
  • 基金资助:
    “有机化学”和“中级有机化学”一流课程建设项目

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 E-mail:jxxu@mail.buct.edu.cn

摘要:

环氧乙烷亲核开环的区域选择性规则是有机化学中典型脂肪三元杂环亲核性开环的选择性规则,具有普遍性。本文以非对称环氧乙烷的亲核性开环为核心,从开环反应过渡态稳定性的角度讨论了决定环氧乙烷亲核开环区域选择性的原因。介绍了该区域选择性规则在经过三元杂环正离子中间体的非对称烯烃亲电加成反应区域选择性教学中的应用。加强学生对不同反应的机理和选择性的联系,起到教学中融会贯通的作用,可以提高教学效率和效果。

关键词: 环氧乙烷, 区域选择性, 亲核开环, 教学, 应用, 规则

Abstract:

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

MSC2000: 

  • G64