苯炔的制备和反应实验的改进与再设计  

Improvement and Redesign of Benzyne Preparation and Reaction Experiments

作　　者：文巍 吴杉 石佳 乔恪凡 郭其祥[1] 吴竹莲[1] WEN Wei;WU Shan;SHI Jia;QIAO Ke-Fan;GUO Qi-Xiang;WU Zhu-Lian(School of Chemistry and Chemical Engineering,Southwest University,Chongqing 400715,China)

机构地区：[1]西南大学化学化工学院,重庆400715

出　　处：《化学教育（中英文）》2024年第8期43-47,共5页Chinese Journal of Chemical Education

基　　金：重庆市高等教育教学改革研究项目(233077);西南大学教育教学改革研究项目(2023JY006)。

摘　　要：苯炔的制备和反应实验同时融合了苯炔和Diels-Alder反应相关知识,是大学有机化学实验教学的重要内容之一。传统的实验方案以邻氨基苯甲酸为原料首先制得取代芳基重氮盐,通过重氮盐的热分解产生苯炔,然后与蒽发生Diels-Alder反应。但邻氨基苯甲酸属于第一类易制毒化学品,为本实验的开展带来不便。同时传统方案还存在诸多不足,如存在潜在的爆炸风险,需要使用到危化品试剂,产品纯化难度大且操作繁琐等。本改进方案通过改变苯炔前体和苯炔捕获试剂克服了原有方案的不足,并且实验原料易得、时长合适、条件温和、反应重复性好,适合本科有机化学实验教学。更为重要的是,通过设计对照实验引入探索性讨论学习内容,有利于学生综合能力的提升和科学思维的培养。Experiments on the preparation and reaction of benzyne include relevant knowledge of benzyne and Diels-Alder reaction,and is an important organic training experiment in universities.In the current experimental plan,anthranilic acid is used as the material to prepare substituted aryl diazonium,which is then thermally decomposed to produce benzyne,and the benzyne undergo Diels-Alder reaction with anthracene.However,anthranilic acid belongs to the category 1 precursor chemicals,and its sales and use are strictly regulated.At the same time,there are many shortcomings in the current experimental plan,such as potential explosion risk,the need to use hazardous chemicals,difficulty in purification and cumbersome operations.The improved experimental scheme overcomes the shortcomings by changing the benzyne precursor and the capture reagent.Moreover,the materials are easily available,the duration is appropriate,the reaction condition is mild,and the reaction is reproducible,making it suitable for undergraduate experiments.In addition,exploratory learning was introduced by the design of controlled experiments.This is beneficial for the improvement of students’comprehensive abilities and the cultivation of scientific thinking.

关 键 词：苯炔 DIELS-ALDER反应 呋喃 实验改进 

分 类 号：O625.12-4[理学—有机化学] G642[理学—化学]