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Perturbation of conjugation in internally solvated allylic lithium compounds: variation of ligand structure. NMR and X-ray crystallography.内溶剂化烯丙基锂化合物中共轭的扰动：配体结构的变化。核磁共振和X射线晶体学。
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Perturbation of conjugation in allylic lithium compounds due to stereochemical control of internal lithium coordination: crystallography, NMR, and calculational studies.通过内部锂配位的立体化学控制对烯丙基锂化合物中共轭作用的扰动：晶体学、核磁共振和计算研究。
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(±)-松节基锂·四甲基乙二胺的优先结晶

Preferential crystallization of (±)-pinenyllithium·TMEDA.

作者信息

Erickson Alexander N, Haltiwanger Curtis, Rahim Masoumeh, Garner Charles M

机构信息

Department of Chemistry, University of Memphis, Memphis, TN 38152, USA.

Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO 80309, USA.

出版信息

Acta Crystallogr C Struct Chem. 2024 Jul 1;80(Pt 7):297-301. doi: 10.1107/S2053229624004662. Epub 2024 Jun 19.

DOI:10.1107/S2053229624004662
PMID:38899749
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11225615/
Abstract

(±)-Pinenyllithium·TMEDA or (tetramethylethylenediamine-κN,N')(η-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptyl)lithium, [Li(CH)(CHN)], is readily prepared from β-pinene, butyllithium and TMEDA, and the racemic material preferentially crystallizes even from 96:4 (92% ee) mixtures of (-)- and (+)-β-pinene, respectively. The structure is monomeric, with the geminal-dimethyl bridge of the bicyclic structure shielding one face of the allyl system, restricting the lithium to the opposite face and preventing the Li-allyl-Li aggregation observed with some other allyllithium systems. The symmetry of the allyl system, bond lengths, bond angles and out-of-plane deviations are compared to existing structures. In addition, a much older structure of this complex is compared to this very recent one.

摘要

（±）-蒎烯锂·TMEDA或（四甲基乙二胺-κN，N′）（η-6,6-二甲基-2-亚甲基双环[3.1.1]庚基）锂，[Li（CH）（CHN）]，可由β-蒎烯、丁基锂和TMEDA轻松制备，即使分别从（-）-和（+）-β-蒎烯的96:4（92%ee）混合物中，外消旋物质也优先结晶。该结构为单体结构，双环结构的偕二甲基桥屏蔽了烯丙基体系的一个面，将锂限制在相对的面上，并防止了在其他一些烯丙基锂体系中观察到的Li-烯丙基-Li聚集。将烯丙基体系的对称性、键长、键角和面外偏差与现有结构进行了比较。此外，还将该配合物一个更老的结构与这个最新的结构进行了比较。