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

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 h...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2024-04, Vol.61 (4), p.556-567
Main Authors: Shilova, Alexandra N., Shatokhina, Nina S., Kondrashov, Evgeniy V.
Format: Article
Language:English
Subjects:
Cycloaddition
Dehydrochlorination
Oxides
Quantum chemistry
Regioselectivity
Steric hindrance
Substrates
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Summary: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.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.4787