{"title":"Cyclopropyl–Allyl Rearrangement of gem-Dibromoycyclopropanes under the Action of Aluminum Carbenoids","authors":"A. V. Yaroslavova, T. P. Zosim, I. R. Ramazanov","doi":"10.1134/s1070428024020118","DOIUrl":null,"url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>It was found for the first time that 2,3-dialkyl-substituted <i>gem</i>-dibromocyclopropanes react with a solution of the aluminum carbenoid Me<sub>2</sub>AlCH<sub>2</sub>I in CH<sub>2</sub>Cl<sub>2</sub> to form substituted bromoalkenes in a good yield. The reaction is sensitive both to the nature of the organoaluminum Lewis acid and to the substitution in <i>gem</i>-dibromocyclopropane. A mechanism of the cyclopropyl–allyl rearrangement was proposed. The free activation energies of the cyclopropyl–allyl rearrangement were calculated by the B3LYP/6-31G(d) method for a number of <i>gem</i>-dibromocyclopropanes and aluminum-containing Lewis acids.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.8000,"publicationDate":"2024-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1134/s1070428024020118","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
It was found for the first time that 2,3-dialkyl-substituted gem-dibromocyclopropanes react with a solution of the aluminum carbenoid Me2AlCH2I in CH2Cl2 to form substituted bromoalkenes in a good yield. The reaction is sensitive both to the nature of the organoaluminum Lewis acid and to the substitution in gem-dibromocyclopropane. A mechanism of the cyclopropyl–allyl rearrangement was proposed. The free activation energies of the cyclopropyl–allyl rearrangement were calculated by the B3LYP/6-31G(d) method for a number of gem-dibromocyclopropanes and aluminum-containing Lewis acids.
期刊介绍：
Russian Journal of Organic Chemistry is an international peer reviewed journal that covers all aspects of modern organic chemistry including organic synthesis, theoretical organic chemistry, structure and mechanism, and the application of organometallic compounds in organic synthesis.
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