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

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Russian Chemical Bulletin Pub Date : 2024-08-31 DOI:10.1007/s11172-024-4308-5

L. I. Tulyabaeva, R. R. Salakhutdinov, T. V. Tyumkina, A. R. Tulyabaev, M. F. Abdullin

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引用次数: 0

摘要

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。

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

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.

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来源期刊

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.