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Air-Stable Disilacyclopropene with a SiC Bond and Its Conversion to Disilacyclopropenylium Ion:  Silicon−Carbon Hybrid 2π-Electron Systems

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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, 42, 12660–12661
Publication Date (Web):September 29, 2007
https://doi.org/10.1021/ja075740n
Copyright © 2007 American Chemical Society
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Abstract

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An air-stable disilacyclopropene with a SiC bond, 1,1,2-tris(tri-tert-butylsilyl)-3-(1-adamantyl)disilacyclopropene (2), was synthesized as yellow crystals by the reaction of (tBu3Si)2SiLi2 (1) with 1-adamantanecarbonyl chloride in THF. The molecular structure of 2 was established by X-ray crystallography. The disilacyclopropene 2 represents the first CSi2 hybrid heavy analogue of cyclopropene featuring a skeletal SiC double bond of 1.745(2) Å. The reaction of 2 with triphenylmethylium tetraarylborate in toluene produced 1,2-bis(tri-tert-butylsilyl)-3-(1-adamantyl)disilacyclopropenylium ion (3+), which was isolated in the form of the tetraarylborate salt as extremely air- and moisture-sensitive yellow crystals, representing the first isolable cyclopropenylium ion derivative with a silicon−carbon hybrid system.

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Experimental procedures and spectral data for 1, 2, 3+·BAr4-, tables of crystallographic data including atomic positional and thermal parameters for 2 (PDF/CIF). This material is available free of charge via the Internet at http://pubs.acs.org.

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