高等学校化学学报

高等学校化学学报 ›› 1987, Vol. 8 ›› Issue (9): 819.

• 研究简报 • 上一篇    下一篇

Meerwein芳基化反应(Ⅰ)--N-乙烯基邻苯二甲酰亚胺的芳基化

胡宏纹, 潘毅, 徐建华   

  1. 南京大学化学系
  • 收稿日期:1986-03-11 出版日期:1987-09-24 发布日期:1987-09-24

Studies on the Meerwein Arylation Reaction(Ⅰ)--Arylation of N-Vinylphthalimide

Hu Hongwen, Pan Yi, Xu Jinghua   

  1. Department of Chemistry, Nanjing University, Nanjing
  • Received:1986-03-11 Online:1987-09-24 Published:1987-09-24

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摘要： Meerwein芳基化反应是在烯键上导入芳基的一种重要方法:ArN2Cl+RCH=CHZ→ArCR=CHZ+ArCHRCHClZ化合物RCH=CHZ中Z为电子取代基时,反应容易进行,Z为OAc、OR时,也可以起芳基化反应,但烯胺(Z=NR2)与芳基重氮盐作用,只得到偶联产物。烯胺与N,N-二烷基苯胺为插烯物(Vinglogs),由于氮原子上的未共电子对与π键共轭,使烯键或苯环碳原子上电子密度增加,容易起偶联反应。

Abstract: N-Vinylphthalimide was treated with aromatic diazonium chlorides ArN2+Cl-<Ar=o-BrC6H4-;p-BrC6H4-;o-ClC6H4-;p-ClC6H4-; 2, 4-Cl2C6H3-; 2,6-C12C6H3-;2,4,6-Br3C6H2-; p-CH,COC6H4-; m-NO C6H4-) in the presence of cuprous chloride to give the corresponding N-(2-ary1-1-chloroethyl) phthalimide.The latter compounds were transformed to N-(2-arylvinyl)phth--alimide by refluxing with N, N-diethylaniline.

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