Cyclopropyl–Allyl Rearrangement of gem-Dibromoycyclopropanes under the Action of Aluminum Carbenoids
IF 0.8
4区 化学
Q4 CHEMISTRY, ORGANIC
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.
在碳化铝作用下 gem-Dibromoy 环丙烷的环丙基烯丙基重排
摘要 首次发现，2,3-二烷基取代的gem-二溴环丙烷与碳化铝Me2AlCH2I在CH2Cl2中的溶液反应生成取代的溴烯烃，产率很高。该反应对有机铝路易斯酸的性质和二溴环丙烷中的取代作用都很敏感。提出了环丙基-烯丙基重排的机理。通过 B3LYP/6-31G(d) 方法计算了多种 gem-dibromocyclopropanes 和含铝 Lewis 酸的环丙基-烯丙基重排自由活化能。
本文章由计算机程序翻译，如有差异，请以英文原文为准。
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来源期刊
CiteScore
1.40
自引率
25.00%
发文量
139
审稿时长
3-6 weeks
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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