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Isolable Alkali-Metal-Substituted Silyl Radicals (tBu2MeSi)2SiM (M = Li, Na, K): Electronically and Sterically Accessible Planar Silyl Radicals

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Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
* To whom correspondence should be addressed. Tel: +81-29-853-4314 . Fax: +81-29-853-4314. E-mail: [email protected]
Cite this: Organometallics 2008, 27, 7, 1358–1360
Publication Date (Web):March 4, 2008
https://doi.org/10.1021/om8000185
Copyright © 2008 American Chemical Society
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Abstract

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Tetrakis(di-tert-butylmethylsilyl)disilene (1) was treated with 2.2 equiv of MNp (metal naphthalenide, M = Na, K) in THF followed by addition of 2 equiv of a crown ether (2b, 15-crown-5; 2c, 18-crown-6), resulting in the formation of the first isolable alkali-metal-substituted silyl radicals 2, which were characterized by both EPR spectra and X-ray crystallography. The lithium-substituted silyl radical 2a was also synthesized as an isolable compound by the reaction of free silylene anion radical with LiBr, and it has a monomeric structure in solution but a dimeric structure in the solid state.

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For 2a−c, text giving experimental procedures and tables and CIF files giving crystallographic data, including atomic positional and thermal parameters. This material is available free of charge via the Internet at http://pubs.acs.org.

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This article is cited by 31 publications.

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  3. Johann Hlina, Christian Mechtler, Harald Wagner, Judith Baumgartner and Christoph Marschner. Multiple Silyl Exchange Reactions: A Way to Spirooligosilanes. Organometallics 2009, 28 (14) , 4065-4071. https://doi.org/10.1021/om900287c
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  16. S.U. Ahmad, S. Inoue. Radicals, Anions, and Cations of Silicon and Silylenes. 2016,,, 27-72. https://doi.org/10.1016/B978-0-12-803530-6.00006-8
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  20. Kanako Taira, Masaaki Ichinohe, Akira Sekiguchi. Isolable Aryl-Substituted Silyl Radicals: Synthesis, Characterization, and Reactivity. Chemistry - A European Journal 2014, 20 (30) , 9342-9348. https://doi.org/10.1002/chem.201402482
  21. Valeri Leich, Kevin Lamberts, Thomas P. Spaniol, Jun Okuda. Crown ether adducts of light alkali metal triphenylsilyls: synthesis, structure and hydrosilylation catalysis. Dalton Trans. 2014, 43 (38) , 14315-14321. https://doi.org/10.1039/C4DT00916A
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