[3+2] Cycloaddition of nitrile oxides to dichloropropenes and 1,3-dichlorobut-2-ene: A regioselectivity issue

被引：0
|
作者：
Shilova, Alexandra N. [1 ]
Shatokhina, Nina S. [1 ]
Kondrashov, Evgeniy V. [1 ,2 ]
机构：
[1] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, Irkutsk, Russia
[2] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, 1 Favorsky St, Irkutsk 664033, Russia
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2024年 / 61卷 / 04期
关键词：
ALDOXIMES; ALKENES;
D O I：
10.1002/jhet.4787
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of nitrile oxides with 2,3-dichloroprop-1-ene, 1,3-dichloroprop-1-ene, and 1,3-dichlorobut-2-ene leads to 5-(chloromethyl)isoxazoles, 4-(chloromethyl)isoxazoles, or to mixtures of both regioisomers. The direction of cycloaddition and reactivity of substrate is determined by the steric hindrance at the terminal carbon atom of the alkene double bond. It has been found that the isomeric products of cycloaddition of nitrile oxides to 1,3-dichloropropene have significantly different dehydrochlorination capabilities. The experimental data on the regioselectivity of cycloaddition and the relative reactivity of substrates are in agreement with the results of quantum chemical calculations. [3 + 2] Cycloaddition of nitrile oxides to chloroalkenes-common organochlorine wastes: experimental and DFT study.image
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页码：556 / 567
页数：12
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