One-pot synthesis of spiro[adamantane-2,2′-boriranes] via the Cp2TiCl2-catalyzed cycloboration of methyleneadamantane with boron halides

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
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,&nbsp;R. R. Salakhutdinov,&nbsp;T. V. Tyumkina,&nbsp;A. R. Tulyabaev,&nbsp;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.

通过 Cp2TiCl2 催化亚甲基金刚烷与卤化硼的环硼化作用,一步合成螺[金刚烷-2,2′-硼环]化合物
通过亚甲基金刚烷与 BF3-THF 和 RBCl2-SMe2(R 为 2-降冰片烷基和环辛基)在 Cp2TiCl2 和 Mg(卤离子的接受体)存在下的催化环硼化反应,开发了一种新的单锅法合成早期未知的含硼金刚烷衍生物--螺[金刚烷-2,2′-环硼烷]。利用一维(1H、13C、11B 和 19F)和二维(HSQC、HMBC、COSY 和扩散有序 (DOSY))核磁共振技术阐明了螺[金刚烷-2,2′-硼烷]的结构。核磁共振技术。根据实验和计算的 11B NMR 化学位移的比较以及络合物形成的热力学参数的计算数据,确定了 1-氟取代的螺[金刚烷-2,2′-环硼烷]与溶剂分子(四氢呋喃)的络合物。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
Russian Chemical Bulletin
Russian Chemical Bulletin 化学-化学综合
CiteScore
2.70
自引率
47.10%
发文量
257
审稿时长
3-8 weeks
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.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信