可见光诱导无金属催化合成邻四氢呋喃基苯乙酮肟醚  

Visible Light-Induced Metal-Free Catalytic Synthesis of Acetophenone o-Tetrahydrofuran-2-Yl Oxime

作　　者：涂梦 刘小睿 尹钰芸 彭嘉琪 白芮华 张伟[1] 沈永淼 Meng Tu;Xiao-Rui Liu;Yu-Yun Yin;Jia-Qi Peng;Rui-Hua Bai;Wei Zhang;Yong-Miao Shen(Department of Chemistry,Zhejiang Sci-Tech University,Hangzhou 310018,China;Key Laboratory of Excited-State Materials of Zhejiang Province,Zhejiang University,Hangzhou 310027,China)

机构地区：[1]浙江理工大学理学院,杭州310018 [2]浙江大学浙江省激发态材料合成与应用重点实验室,杭州310027

出　　处：《大学化学》2023年第5期211-219,共9页University Chemistry

基　　金：浙江省激发态材料合成与应用重点实验室(2021E10002);浙江省“十三五”省级大学生校外实践基地建设项目(SXWJD1);应用化学国家一流本科专业建设项目;浙江理工大学科研启动基金(18062144-Y);浙江理工大学-肯特催化材料股份有限公司研究生联合培养基地(11430731732226)。

摘　　要：自由基反应作为有机化学的三大基本机理之一在实验教学中被长期忽略,造成理论与实践的脱节。本课题以苯乙酮肟和四氢呋喃为起始原料,在3 W蓝色LED光照下,由四溴化碳介导的经自由基历程构建C―O键合成邻四氢呋喃基苯乙酮肟醚,并利用核磁、红外、紫外手段对产物进行表征。本合成实验所需的设备简单、廉价,反应条件温和,且实验开设的普适性高。通过本实验的学习不仅可以让学生学习到溴自由基在有机合成中的应用,使学生能更好地理解和掌握自由基反应的过程,而且还能通过产物分子结构的分析,提高学生综合解谱的能力。As one of the three basic mechanisms in organic chemistry,the free radical reaction,has been neglected for a long time in experimental teaching,which has led to a disconnection between theory and practice.In this study,o-tetrahydrofuranyl acetophenone oxime ether was synthesized from acetophenone oxime and tetrahydrofuran by a free radical process mediated by carbon tetrachloride under 3 W blue LED light.The products were characterized by NMR,IR and UV spectroscopy.This experiment only requires simple and inexpensive equipment and mild reaction conditions,and has high universality.It teaches the application of bromine radicals in organic synthesis so that students can master their understanding of free radical reactions,and allows them to improve their practical skills by analyzing the molecular structure of the product.

关 键 词：苯乙酮肟醚 自由基反应 可见光催化 C―O键形成 四溴化碳 

分 类 号：G64[文化科学—高等教育学] O6[文化科学—教育学]