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Hydroboration of Disilyne RSi≡SiR (R = SiiPr[CH(SiMe3)2]2), Giving Boryl-Substituted Disilenes

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Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
*Phone: +81-29-853-4314. Fax: +81-29-853-4314 E-mail: [email protected]
Cite this: Organometallics 2011, 30, 7, 2044–2050
Publication Date (Web):March 15, 2011
https://doi.org/10.1021/om200106h
Copyright © 2011 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 hydroboranes afforded boryl-substituted disilenes R(R′2B)Si═SiHR 3a and 3b (R = SiiPr[CH(SiMe3)2]2, R′2B = 9-borabicyclo[3.3.1]nonan-9-yl (3a), catecholboryl (3b)). Spectroscopic and X-ray crystallographic analyses of 3a and 3b showed that 3a has a nearly coplanar arrangement of the Si═Si double bond and the boryl group, allowing π-conjugation between them, whereas 3b, with a markedly twisted arrangement, exhibits no such conjugation. Theoretical calculations suggest that π-conjugation between the π-orbital of the Si═Si double bond and the vacant 2p-orbital on the boron atom is markedly influenced by the dihedral angle between the Si═Si double-bond plane and boryl group plane.

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Tables of crystallographic data including atomic positional and thermal parameters for 3b (PDF/CIF) and computational details (tables of atomic coordinates for optimized geometries of the model compound 3′ and values of their total energies). This material is available free of charge via the Internet at http://pubs.acs.org.

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Cited By

This article is cited by 37 publications.

  1. Zhaocai Liu, Jianying Zhang, Hao Yang, Chunming Cui. Synthesis of Boryl-Substituted Disilane, Disilene, and Silyl Cation. Organometallics 2020, 39 (23) , 4164-4168. https://doi.org/10.1021/acs.organomet.0c00148
  2. Miao Tian, Jianying Zhang, Hao Yang, Chunming Cui. Isolation of a 1-Magnesium-2,3-disilacyclopropene and a Related Bis(disilenide). Journal of the American Chemical Society 2020, 142 (9) , 4131-4135. https://doi.org/10.1021/jacs.0c00519
  3. Tomoyuki Kosai and Takeaki Iwamoto . Stable Push–Pull Disilene: Substantial Donor–Acceptor Interactions through the Si═Si Double Bond. Journal of the American Chemical Society 2017, 139 (50) , 18146-18149. https://doi.org/10.1021/jacs.7b09989
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