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Download Hi-Res ImageDownload to MS-PowerPointCite This:Organometallics 2008, 27, 14, 3325-3327
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1,2-Bis(ferrocenyl)disilene: A Multistep Redox System with an Si═Si Double Bond

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Institute of Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan, and Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo, Japan
* To whom correspondence should be addressed. Tel: +81-774-38-3200. Fax: +81-774-38-3209. E-mail: [email protected]
†Kyoto University.
‡Waseda University.
Cite this: Organometallics 2008, 27, 14, 3325–3327
Publication Date (Web):June 24, 2008
https://doi.org/10.1021/om8003543
Copyright © 2008 American Chemical Society
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Abstract

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A new type of disilene substituted by ferrocenyl groups, 1,2-bis(ferrocenyl)disilene, was synthesized as a good candidate for a novel d−π electron system, and the unique properties of the Si═Si π bond of this new disilene were revealed. On the basis of the results of the electrochemical analyses, 1,2-Tip2-1,2-Fc2-disilene (Tip = 2,4,6-triisopropylphenyl, Fc = ferrocenyl) was found to be a stable five-electron redox system with four steps.

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Text, tables, and figures giving experimental procedures and spectral data for new compounds and CIF files giving X-ray data for 1 and 2. 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 44 publications.

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  2. Naoki Hayakawa, Shogo Nishimura, Nobuhiro Kazusa, Nozomu Shintani, Tsukasa Nakahodo, Hisashi Fujihara, Manabu Hoshino, Daisuke Hashizume, and Tsukasa Matsuo . π-Conjugation between a Si═Si Double Bond and Thiophene Rings: Synthesis, Structural Characteristics, and Photophysical Properties of 1,2-Bis(thiophen-2-yl)disilene and 1,2-Bis(2,2′-bithiophen-5-yl)disilene. Organometallics 2017, 36 (17) , 3226-3233. https://doi.org/10.1021/acs.organomet.7b00370
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  23. Norihiro Tokitoh, Yoshiyuki Mizuhata, Yasunobu Egawa, Takahiro Sasamori. Synthesis of 1,2-Dialkynyldisilanes Incorporated in 10-Membered-Ring System. HETEROCYCLES 2015, 90 (2) , 1111. https://doi.org/10.3987/COM-14-S(K)81
  24. Megumi Kobayashi, Naoki Hayakawa, Koichi Nakabayashi, Tsukasa Matsuo, Daisuke Hashizume, Hiroyuki Fueno, Kazuyoshi Tanaka, Kohei Tamao. Highly Coplanar ( E )-1,2-Di(1-naphthyl)disilene Involving a Distinct CH–π Interaction with the Perpendicularly Oriented Protecting Eind Group. Chemistry Letters 2014, 43 (4) , 432-434. https://doi.org/10.1246/cl.131043
  25. Takahiro Sasamori. The Synthesis and Properties of Bimetallic d-^|^pi; Electron Systems Containing Metallocenyl Substituents of Fe or Ru, and ^|^pi;-Electron Spacers of Heavier Main Group Elements from Group 14 or 15. Journal of Synthetic Organic Chemistry, Japan 2014, 72 (11) , 1279-1289. https://doi.org/10.5059/yukigoseikyokaishi.72.1279
  26. José A. Gámez, Markus Hermann, Gernot Frenking. Structures and Bonding Situation of the Allyl Systems and Cyclic Isomers [H 2 E - E (H)- E H 2 ] -,·,+ ( E = C, Si, Ge, Sn). Zeitschrift für anorganische und allgemeine Chemie 2013, 639 (14) , 2493-2501. https://doi.org/10.1002/zaac.201300473
  27. Takahiro Sasamori, Norihiro Tokitoh. A New Family of Multiple-Bond Compounds between Heavier Group 14 Elements. Bulletin of the Chemical Society of Japan 2013, 86 (9) , 1005-1021. https://doi.org/10.1246/bcsj.20130134
  28. Michiyasu Sakagami, Takahiro Sasamori, Heisuke Sakai, Yukio Furukawa, Norihiro Tokitoh. 1,2-Bis(ferrocenyl)-Substituted Distibene and Dibismuthene: SbSb and BiBi Units as π Spacers between Two Ferrocenyl Units. Chemistry - An Asian Journal 2013, 8 (4) , 690-693. https://doi.org/10.1002/asia.201201227
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  33. Wenyuan Wang, Shigeyoshi Inoue, Stephan Enthaler, Matthias Driess. Bis(silylenyl)- and Bis(germylenyl)-Substituted Ferrocenes: Synthesis, Structure, and Catalytic Applications of Bidentate Silicon(II)-Cobalt Complexes. Angewandte Chemie 2012, 124 (25) , 6271-6275. https://doi.org/10.1002/ange.201202175
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  35. Norihiro Tokitoh, Akihiro Yuasa, Takahiro Sasamori. Chalcogenation of 1,2-Bis(ferrocenyl)disilene: The First Isolation of 1,2,3,4-Dithiadisiletane. Phosphorus, Sulfur, and Silicon and the Related Elements 2011, 186 (5) , 1217-1219. https://doi.org/10.1080/10426507.2010.507730
  36. Tsukasa Matsuo, Baolin Li, Kohei Tamao. π-conjugated phosphasilenes stabilized by fused-ring bulky “Rind” groups. Comptes Rendus Chimie 2010, 13 (8-9) , 1104-1110. https://doi.org/10.1016/j.crci.2010.07.005
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  44. Yuzhong Wang, Gregory H. Robinson. Unique homonuclear multiple bonding in main group compounds. Chemical Communications 2009, 32 (35) , 5201. https://doi.org/10.1039/b908048a

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