文献类型：期刊文献

英文题名：Hypervalent Iodonium Zwitterions and Nucleophilic Aromatic Substitution: A Multiple-Step Experiment in Organic Chemistry

作者：Han, Jianwei[1,2,3];Chen, Huangguan[1,2,3];An, Guoqiang[1,2,3];Sun, Xiaoya[1,2,3];Li, Xiangyu[1,2,3];Liu, Yiwu[1,2,3];Zhao, Sijia[1,2,3];Wang, Limin[1,2,3]

机构：[1]East China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Feringa Nobel Prize Scientist Joint Res Ctr, Dept Fine Chem, Shanghai 200237, Peoples R China;[3]East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, Shanghai 200237, Peoples R China

年份：2021

卷号：98

期号：12

起止页码：3992

外文期刊名：JOURNAL OF CHEMICAL EDUCATION

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000731641200045)】；

基金：This work was supported by the Emerging Engineering Education (3E) program for Fine Chemical Engineering and Molecular Engineering project at East China University of Science and Technology by the Ministry of Education of China; Natural Science Foundation of Shanghai (20ZR1413500) and National Nature Science Foundation of China (NSFC 21772039, 21472213), Shanghai Municipal Science and Technology Major Project (Grant No. 2018SHZDZX03). We gratefully acknowledge Prof. Dr. Ullrich Englert (RWTH Aachen University) for the proofreading and helpful suggestions.

语种：英文

外文关键词：First-year Graduate; Upper-Division Undergraduate; Organic Chemistry; Hands-on Learning; Manipulatives; Aromatic Compounds; Nucleophilic Substitution

摘要：Iodonium zwitterions are hypervalent iodine compounds in which the iodine center binds to two substituents and carries a positive formal charge which is compensated by a negative charge within the same molecule. Under thermodynamic conditions, iodonium zwitterions allow concerted nucleophilic aromatic substitutions to be performed, followed by rearrangement reactions. In general, nucleophilic aromatic substitutions proceed stepwise, either via an elimination-addition or via an addition- elimination pathway. It has been suggested that nucleophilic aromatic substitutions occur through a transition state which reduces the activation barrier by charge delocalization. The laboratory experiments reported here aim to give students better insight into the concepts of nucleophilic aromatic substitutions and iodonium zwitterions. These experiments can be used to demonstrate a series of important topics and experimental skills in organic chemistry. In addition, they also teach students analytical techniques such as NMR spectroscopy, mass spectrometry, and X-ray diffraction.