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Updated: Jun 1, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
(μ-1,4,7,10-Tetra-oxacyclo-dodeca-ne)bis-[(1,4,7,10-tetra-oxacyclo-dodeca-ne)lithium] bis-(perchlorate)
Abstract:
12-Crown-4 ether (12C4) and LiClO(4) combine to form the ionic title compound, [Li(2)(C(8)H(16)O(4))(3)](ClO(4))(2), which is com-posed of discrete Li/12C4 cations and perchlorate anions. In the [Li(2)(12C4)(3)](2+) cation there are two peripheral 12C4 ligands, which each form four Li-O bonds with only one Li(+) atom. Additionally there is a central 12C4 in which diagonal O atoms form one Li-O bond each with both Li(+) atoms. Therefore each Li(+) atom is penta-coordinated in a distorted square-pyramidal geometry, forming four longer bonds to the O atoms on the peripheral 12C4 and one shorter bond to an O atom of the central 12C4. The cation occupies a crystallographic inversion centre located at the center of the ring of the central 12C4 ligand. The Li(+) atom lies above the cavity of the peripheral 12C4 by 0.815 (2) Å because it is too large to fit in the cavity.
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