E. V. Shulishov, O. A. Pantyukh, E. D. Streltsova, L. G. Menchikov, Yu. V. Tomilov
{"title":"Catalytic reaction of dicyclopropylacetylene with diazomethane: synthesis of ivyane[4]","authors":"E. V. Shulishov, O. A. Pantyukh, E. D. Streltsova, L. G. Menchikov, Yu. V. Tomilov","doi":"10.1007/s11172-025-4580-z","DOIUrl":null,"url":null,"abstract":"<div><p>The reaction of dicyclopropylacetylene with excess diazomethane in the presence of copper compounds leads successively first to dicyclopropylcyclopropene resulting from multiple bond cyclopropanation and then to 1,3-dicyclopropylbicyclo[1.1.0]butane. The latter under the reaction conditions partially isomerizes to 2,3-dicyclopropylbuta-1,3-diene, which, in turn, undergoes further cyclopropanation. As a result, when an 8–10-fold excess of diazomethane is used, a hydrocarbon of the 1,1-oligocyclopropane series, 1,1′-dicyclopropylbicyclopropane (ivyane[4]), is formed. Monocyclopropanation of dicyclopropylbutadiene readily proceeds in the presence of Pd(acac)<sub>2</sub>, whereas cyclopropanation of the second double bond occurs only with a large excess of diazomethane.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 3","pages":"865 - 870"},"PeriodicalIF":1.7000,"publicationDate":"2025-04-28","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/s11172-025-4580-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
The reaction of dicyclopropylacetylene with excess diazomethane in the presence of copper compounds leads successively first to dicyclopropylcyclopropene resulting from multiple bond cyclopropanation and then to 1,3-dicyclopropylbicyclo[1.1.0]butane. The latter under the reaction conditions partially isomerizes to 2,3-dicyclopropylbuta-1,3-diene, which, in turn, undergoes further cyclopropanation. As a result, when an 8–10-fold excess of diazomethane is used, a hydrocarbon of the 1,1-oligocyclopropane series, 1,1′-dicyclopropylbicyclopropane (ivyane[4]), is formed. Monocyclopropanation of dicyclopropylbutadiene readily proceeds in the presence of Pd(acac)2, whereas cyclopropanation of the second double bond occurs only with a large excess of diazomethane.
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.
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
