Intramolecular 1,3-Dipolar Cycloaddition of Nitrile N-Oxide Accompanied by Dearomatization

被引：37
|
作者：
Yonekawa, Morio [1 ]
Koyama, Yasuhito [1 ]
Kuwata, Shigeki [2 ]
Takata, Toshikazu [1 ]
机构：
[1] Tokyo Inst Technol, Dept Organ & Polymer Mat, Tokyo 1528552, Japan
[2] Tokyo Inst Technol, Dept Appl Chem, Tokyo 1528552, Japan
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 04期
关键词：
POLYCYCLIC AROMATIC-HYDROCARBONS; CLICK POLYMERIZATION; DERIVATIVES; REACTIVITY;
D O I：
10.1021/ol300125s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Intramolecular 1,3-dipolar cycloaddition of 2-phenoxybenzonitrile N-oxides to benzene rings, accompanied by dearomatization, formed the corresponding isoxazolines in high yields. The X-ray single-crystal structure analysis revealed that the reaction formed the cis-adduct as a single isomer. The substituents on the benzene rings markedly affected the reaction rate, yield, and structure of the final product.
引用
收藏
页码：1164 / 1167
页数：4
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