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Reactivity of a Disilyne RSi≡SiR (R = SiiPr[CH(SiMe3)2]2) toward π-Bonds:  Stereospecific Addition and a New Route to an Isolable 1,2-Disilabenzene

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Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan, and Department of Theoretical Molecular Science, Institute for Molecular Science, Okazaki 444-8585, Japan
Cite this: J. Am. Chem. Soc. 2007, 129, 25, 7766–7767
Publication Date (Web):June 2, 2007
https://doi.org/10.1021/ja072759h
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 cis- and trans-butenes produced cis- and trans-3,4-dimethyl-1,2-disilacyclobutenes 2a and 2b, respectively. The reactions proceeded in a stereospecific manner. Theoretical calculations on the reaction between 1 and 2-butenes show that the reaction proceeds via the interaction between the LUMO (πin*) of 1 and the HOMO of 2-butene, resulting in a formal [1 + 2] cycloaddition to give the silacyclopropyl−silylene intermediate, followed by its ring expansion to produce the final product. The reaction of 1 with phenylacetylene produced 1,2-disilabenzene derivative as a mixture of the two regioisomers, one of them being characterized by X-ray crystallography. The six-membered ring of 1,2-disilabenzene of 3a is almost planar with an Si−Si bond length of 2.2018(18) Å and Si−C bond lengths of 1.804(4) and 1.799(5) Å.

§

 University of Tsukuba.

*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

‡

 Institute for Molecular Science.

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The experimental procedures of 2a, 2b, 3a, and 3b;, table of crystallographic data including atomic positional and thermal parameters for 2b and 3a (PDF/CIF); calculated energies of transition states and intermediates for the reaction of 1 with acetylene. This material is available free of charge via the Internet at http://pubs.acs.org.

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