亲核性1,2-重排为何迁移基团的构型保持不变  

Why Do the Chiral Shift Groups Keep Their Configuration in the Nucleophilic 1,2-Rearrangements

作　　者：许家喜 麻远[2] XU Jia-Xi;MA Yuan(College of Chemistry,Beijing University of Chemical Technology,Beijing 100029,China;Department of Chemistry,Tsinghua University,Beijing 100084,China)

机构地区：[1]北京化工大学化学学院,北京100029 [2]清华大学化学系,北京100084

出　　处：《化学教育（中英文）》2022年第24期115-119,共5页Chinese Journal of Chemical Education

基　　金：有机化学本科育人团队项目;有机化学和中级有机化学一流课程建设项目。

摘　　要：亲核性1,2-重排反应是有机化学的重要反应之一,重排中离去基团的离去和迁移基团的迁移步骤既可以是分步的,也可以是协同的,但是迁移基团的构型始终保持不变。本文用超共轭效应和反应过程中有机立体电子效应解释了此现象,掌握一般规律,希望能够从教学上便于教师讲授和学生学习理解。Nucleophilic 1,2-rearrangements are one class of important organic reactions.Leaving of the leaving groups and shift of the shift groups can be either stepwise or concerted.However,the rearrangements always occur with retention of the configuration at the migrating carbon of the shift groups.This article introduces using hyperconjugation and stereoelectronic effect to explain the phenomenon and to grasp the general rule,hoping to provide help for teachers’teaching and students’understanding in teaching and learning organic chemistry.

关 键 词：亲核性重排反应 迁移 重排反应 超共轭效应 立体电子效应 构型保持 

分 类 号：O621.259.3[理学—有机化学]