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An Isolable Disilyne Anion Radical and a New Route to the Disilenide Ion upon Reduction of a Disilyne

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Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
Cite this: J. Am. Chem. Soc. 2007, 129, 1, 26–27
Publication Date (Web):December 15, 2006
https://doi.org/10.1021/ja066762x
Copyright © 2007 American Chemical Society
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Abstract

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The reaction of 1,1,4,4-tetrakis[bis(trimethylsilyl)methyl]-1,4-diisopropyltetrasila-2-yne 1 with tBuLi produced disilenyllithium derivative 2, the product of the formal addition of LiH across the Si⋮Si triple bond through a single electron transfer reaction. The solvent-separated ion pair of the disilenide 3 was characterized by X-ray crystallography. The bulky SiiPr[CH(SiMe3)2]2 groups are arranged in the trans fashion with a silicon−silicon double bond length of 2.2034(9) Å. The reaction of 1 with an equivalent amount of potassium graphite (KC8) in THF produced the disilyne anion radical 4, which was isolated in the form of its potassium salt as extremely air- and moisture-sensitive dark brown crystals. The molecular structure of 4 was established by X-ray crystallography, which showed a trans-bent structure (av 113.4°) with the central Si−Si bond length of 2.1728(14) Å. An electron spin resonance (ESR) study indicates delocalization of the unpaired electron between the two central silicon atoms of 4.

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Experimental procedures of 2−4, tables of crystallographic data including atomic positional and thermal parameters for 3 and 4 (PDF/CIF), optimized geometries and GIAO calculations on H3Si(H)SiSi(SiH3)Li(OMe2)3, π-MO diagram, and energies of molecular orbitals of 4. This material is available free of charge via the Internet at http://pubs.acs.org.

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