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Cyclobutadiene Dianions Consisting of Heavier Group 14 Elements:  Synthesis and Characterization

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Department of Chemistry, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
Cite this: J. Am. Chem. Soc. 2004, 126, 15, 4758–4759
Publication Date (Web):March 24, 2004
https://doi.org/10.1021/ja030662z
Copyright © 2004 American Chemical Society
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Abstract

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The first “heavy” cyclobutadiene dianions (CBD2-), tetrakis(di-tert-butylmethylsilyl)-1,2-disila-3,4-digermacyclobutadiene dianion 22- and tetrakis(di-tert-butylmethylsilyl)tetrasilacyclobutadiene dianion 42-, have been synthesized by the reductive dehalogenation of the corresponding precursors with potassium graphite in THF. Structural characterization of [K+(thf)2]2·22- and [K+(thf)2]2·42- has been achieved by X-ray crystallography, showing that the central four-membered ring is significantly folded and has two η2-1,3-coordinated potassium cations accommodated above and below the ring. The “heavy” CBD2-'s 22- and 42- were found to be nonaromatic compounds, a conclusion that was supported by nucleus-independent chemical shift (NICS) calculations showing a lack of diatropic ring current effects.

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Experimental procedures, spectral data of 22- and 42-, and tables of crystallographic data including atomic positional and thermal parameters for [K+(thf)2]2·42- (PDF). X-ray crystallographic files in CIF format. This material is available free of charge via the Internet at http://pubs.acs.org.

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