The Puzzle of the Regioselectivity and Molecular Mechanism of the (3+2) Cycloaddition Reaction Between E-2-(Trimethylsilyl)-1-Nitroethene and Arylonitrile N-Oxides: Molecular Electron Density Theory (MEDT) Quantumchemical Study

被引：1

作者：

Sadowski, Mikolaj ^{[1
]}

Dresler, Ewa ^{[2
]}

Jasinski, Radomir ^{[1
]}

机构：

[1] Cracow Univ Technol, Dept Organ Chem & Technol, Warszawska 24, PL-31155 Krakow, Poland

[2] Inst Heavy Organ Synth Blachown, Lukasiewicz Res Network, Energetykow 9, PL-47225 Kedzierzyn Kozle, Poland

来源：

MOLECULES | 2025年 / 30卷 / 04期

关键词：

(3+2) cycloaddition; nitrile N-oxides; mechanism; DFT; MEDT; DER-WAALS COMPLEXES; 1,3-DIPOLAR CYCLOADDITION; ORIENTATION; ISOXAZOLES;

D O I：

10.3390/molecules30040974

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The regioselectivity and molecular mechanism of the (3+2) cycloaddition reaction between E-2-(trimethylsilyl)-1-nitroethene and arylonitrile N-oxides were explored on the basis of the omega B97XD/6-311+G(d) (PCM) quantumchemical calculations. It was found that the earlier postulate regarding the regioselectivity of the cycloaddition stage should be undermined. Within our research, several aspects of the title reaction were also examined: interactions between reagents, electronic structures of alkenes and nitrile oxides, the nature of transition states, the influence of the polarity solvent on the reaction selectivity and mechanism, substituent effects, etc. The obtained results offer a general conclusion for all of the important aspects of some groups of cycloaddition processes.

引用

页数：17

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