Yu. M. Selivantev, V. S. Mityanov, E. S. Uvarova, F. A. Kolokolov, A. N. Morozov, O. A. Raitman
{"title":"Interaction of 2-unsubstituted imidazole N-oxides with electron-deficient olefins: a quantum chemical analysis","authors":"Yu. M. Selivantev, V. S. Mityanov, E. S. Uvarova, F. A. Kolokolov, A. N. Morozov, O. A. Raitman","doi":"10.1007/s11172-024-4370-z","DOIUrl":null,"url":null,"abstract":"<div><p>Reactions between the model compound <i>N</i>-1,4,5-trimethyl-1<i>H</i>-imidazole-3-oxide and electron-deficient olefins including 2-(4-methoxybenzylidene)malononitrile, (<i>E</i>)-ethyl-2-cyano-3-(4-methoxyphenyl)acrylate, 2-benzoyl-3-(4-methoxyphenyl)acrylonitrile, and 5-(4-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione were theoretically studied in terms of the density functional theory. It was demonstrated that the reactions can proceed either by the 1,3-dipolar cycloaddition mechanism or by the Michael addition mechanism depending on the type of electron-withdrawing substituents in the olefin molecule. The reaction pathways were calculated and the intermediate structures were determined.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2024-10-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Chemical Bulletin","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s11172-024-4370-z","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Reactions between the model compound N-1,4,5-trimethyl-1H-imidazole-3-oxide and electron-deficient olefins including 2-(4-methoxybenzylidene)malononitrile, (E)-ethyl-2-cyano-3-(4-methoxyphenyl)acrylate, 2-benzoyl-3-(4-methoxyphenyl)acrylonitrile, and 5-(4-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione were theoretically studied in terms of the density functional theory. It was demonstrated that the reactions can proceed either by the 1,3-dipolar cycloaddition mechanism or by the Michael addition mechanism depending on the type of electron-withdrawing substituents in the olefin molecule. The reaction pathways were calculated and the intermediate structures were determined.
期刊介绍：
Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections:
General and Inorganic Chemistry;
Physical Chemistry;
Organic Chemistry;
Organometallic Chemistry;
Chemistry of Natural Compounds and Bioorganic Chemistry.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
