L. I. Tulyabaeva, R. R. Salakhutdinov, T. V. Tyumkina, A. R. Tulyabaev, M. F. Abdullin
{"title":"One-pot synthesis of spiro[adamantane-2,2′-boriranes] via the Cp2TiCl2-catalyzed cycloboration of methyleneadamantane with boron halides","authors":"L. I. Tulyabaeva, R. R. Salakhutdinov, T. V. Tyumkina, A. R. Tulyabaev, M. F. Abdullin","doi":"10.1007/s11172-024-4308-5","DOIUrl":null,"url":null,"abstract":"<div><p>A new one-pot method for the synthesis of earlier unknown boron-containing adamantane derivatives, spiro[adamantane-2,2′-boriranes], <i>via</i> the catalytic cycloboration of methyleneadamantane with BF<sub>3</sub>·THF and RBCl<sub>2</sub>·SMe<sub>2</sub> (R is 2-norbornyl and cyclooctyl) in the presence of Cp<sub>2</sub>TiCl<sub>2</sub> and Mg (acceptor of halide ions) was developed. The structure of spiro[adamantane-2,2′-boriranes] was elucidated using 1D (<sup>1</sup>H, <sup>13</sup>C, <sup>11</sup>B, and <sup>19</sup>F) and 2D (HSQC, HMBC, COSY, and diffusion-ordered (DOSY)) NMR techniques. 1-Fluorosubstituted spiro[adamantane-2,2′-borirane] was identified as a complex with the solvent molecule (THF) according to a comparison of the experimental and calculated <sup>11</sup>B NMR chemical shifts and the calculation data for the thermodynamic parameters of complex formation.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 7","pages":"1907 - 1915"},"PeriodicalIF":1.7000,"publicationDate":"2024-08-31","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/s11172-024-4308-5","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
A new one-pot method for the synthesis of earlier unknown boron-containing adamantane derivatives, spiro[adamantane-2,2′-boriranes], via the catalytic cycloboration of methyleneadamantane with BF3·THF and RBCl2·SMe2 (R is 2-norbornyl and cyclooctyl) in the presence of Cp2TiCl2 and Mg (acceptor of halide ions) was developed. The structure of spiro[adamantane-2,2′-boriranes] was elucidated using 1D (1H, 13C, 11B, and 19F) and 2D (HSQC, HMBC, COSY, and diffusion-ordered (DOSY)) NMR techniques. 1-Fluorosubstituted spiro[adamantane-2,2′-borirane] was identified as a complex with the solvent molecule (THF) according to a comparison of the experimental and calculated 11B NMR chemical shifts and the calculation data for the thermodynamic parameters of complex formation.
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.