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Download Hi-Res ImageDownload to MS-PowerPointCite This:Organometallics 2012, 31, 10, 3904-3910
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1,2-Bis(ferrocenyl)digermene: A d−π Electron System Containing a Ge═Ge Unit

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† Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan
‡ Department of Chemistry & Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan
*Tel: +81-774-38-3202. Fax: +81-774-38-3209. E-mail: [email protected] (T.S.); [email protected] (N.T.).
Cite this: Organometallics 2012, 31, 10, 3904–3910
Publication Date (Web):May 8, 2012
https://doi.org/10.1021/om300064q
Copyright © 2012 American Chemical Society
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Abstract

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The synthesis and structural analysis of the 1,2-bis(ferrocenyl)digermene (E)-Tip(Fc)Ge═Ge(Fc)Tip (Tip = 2,4,6-triisopropylphenyl, Fc = ferrocenyl), a stable crystalline compound, is reported. In this digermene, two ferrocenyl d electron systems are bridged by a Ge═Ge π spacer. As is evident from X-ray crystallographic, spectroscopic, and electrochemical analysis, this 1,2-bis(ferrocenyl)digermene shows effective d−π interaction and the Ge═Ge π bond is stable in the solid state. The Ge═Ge double bond is cleaved at elevated temperatures in the presence of butadiene, with concomitant loss of the π conjugation in the molecule.

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Tables giving X-ray crystallographic data and Cartesian coordinates of the optimized structure of 2 and CIF files giving X-ray crystallographic data. 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 22 publications.

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  2. Tomohiro Sugahara, Takahiro Sasamori, Norihiro Tokitoh. 2,5-Digermaselenophenes: Germanium Analogues of Selenophenes. Journal of the American Chemical Society 2018, 140 (36) , 11206-11209. https://doi.org/10.1021/jacs.8b07588
  3. Anukul Jana, Volker Huch, Henry S. Rzepa, and David Scheschkewitz . A Molecular Complex with a Formally Neutral Iron Germanide Motif (Fe2Ge2). Organometallics 2015, 34 (11) , 2130-2133. https://doi.org/10.1021/om501286g
  4. Thomas Hafner, Ana Torvisco, Michael Traxler, Melanie Wolf, Frank Uhlig. Selective Chlorination of Germanium Hydrides. Zeitschrift für anorganische und allgemeine Chemie 2020, 646 (23-24) , 1876-1881. https://doi.org/10.1002/zaac.202000318
  5. Takahiro Sasamori. Ferrocenyl-substituted low-coordinated heavier group 14 elements. Dalton Transactions 2020, 49 (24) , 8029-8035. https://doi.org/10.1039/D0DT01426E
  6. Koh Sugamata, Shogo Morisako, Takahiro Sasamori. Three-Membered Rings With Two Heteroatoms Including Selenium or Tellurium; Three-Membered Rings With Three Heteroatoms. 2020,,https://doi.org/10.1016/B978-0-12-818655-8.00033-0
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  8. Rinat R. Aysin, Sergey S. Bukalov, Larissa A. Leites, Vladimir Ya Lee, Akira Sekiguchi. Electronic structure and conformational isomerism of the digermene (tBu2MeSi)2Ge=Ge(SiMetBu2)2 as studied by temperature-dependent Raman and UV–vis spectra and quantum-chemistry calculations. Journal of Organometallic Chemistry 2019, 892 , 18-23. https://doi.org/10.1016/j.jorganchem.2019.04.014
  9. Jiří Böserle, Roman Jambor, Milan Erben, Filip Horký, Petr Štěpnička, Aleš Růžička, Libor Dostál. Reactivity of an N , N -Chelated Germylene Toward Substituted Alkynes, Alkenes, and Allenes. Zeitschrift für anorganische und allgemeine Chemie 2019, 645 (9) , 671-678. https://doi.org/10.1002/zaac.201800489
  10. Kirill V. Zaitsev, Kevin Lam, Viktor A. Tafeenko, Alexander A. Korlyukov, Oleg Kh. Poleshchuk. Aryl Oligogermanes as Ligands for Transition Metal Complexes. European Journal of Inorganic Chemistry 2018, 2018 (45) , 4911-4924. https://doi.org/10.1002/ejic.201801095
  11. Christoph Förster, Patrick M. Becker, Katja Heinze. A Ferrocenyl Amino Substituted Stannylene as an Intramolecular Fe→Sn Lewis Adduct. Zeitschrift für anorganische und allgemeine Chemie 2018, 644 (17) , 1057-1063. https://doi.org/10.1002/zaac.201800269
  12. Yuko Suzuki, Takahiro Sasamori, Jing-Dong Guo, Norihiro Tokitoh. A Redox-Active Bis(ferrocenyl)germylene and Its Reactivity. Chemistry - A European Journal 2018, 24 (2) , 364-368. https://doi.org/10.1002/chem.201705598
  13. Jiří Böserle, Roman Jambor, Aleš Růžička, Libor Dostál. Insertion of the N,B,N -chelated germylene into P-Cl Bond(s) in selected chlorophosphines. Journal of Organometallic Chemistry 2018, 855 , 44-50. https://doi.org/10.1016/j.jorganchem.2017.12.018
  14. Hsu-Cheng Hua, Ming-Der Su. Mechanistic investigations and molecular properties of 1,2-bis(ferrocenyl)dimetallenes including group 14 elements. RSC Advances 2017, 7 (71) , 44724-44734. https://doi.org/10.1039/C7RA04935H
  15. Jiří Böserle, Mercedes Alonso, Roman Jambor, Aleš Růžička, Libor Dostál. Synthesis and reactivity of a germylene stabilized by a boraguanidinate ligand. RSC Advances 2016, 6 (23) , 19377-19388. https://doi.org/10.1039/C6RA01187J
  16. Johann Hlina, Judith Baumgartner, Christoph Marschner, Lena Albers, Thomas Müller, Viatcheslav V. Jouikov. Formation and Properties of a Bicyclic Silylated Digermene. Chemistry - A European Journal 2014, 20 (30) , 9357-9366. https://doi.org/10.1002/chem.201402785
  17. 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
  18. Michiyasu Sakagami, Takahiro Sasamori, Heisuke Sakai, Yukio Furukawa, Norihiro Tokitoh. 1,2-Bis(ferrocenyl)dipnictenes: Bimetallic Systems with a Pn=Pn Heavy π-Spacer (Pn: P, Sb, and Bi). Bulletin of the Chemical Society of Japan 2013, 86 (10) , 1132-1143. https://doi.org/10.1246/bcsj.20130174
  19. Zoltán Varga, Magdolna Hargittai. Group 14 structural variations: perhalo derivatives of the “dimetallenes”: dicarbenes, disilenes, digermenes, distannenes, and diplumbenes. Structural Chemistry 2013, 24 (3) , 837-850. https://doi.org/10.1007/s11224-012-0194-9
  20. 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
  21. Jonathan Parr. Carbon, silicon, germanium, tin and lead. Annual Reports Section "A" (Inorganic Chemistry) 2013, 109 , 53. https://doi.org/10.1039/c3ic90019c
  22. Takahiro Sasamori, Michiyasu Sakagami, Masatoshi Niwa, Heisuke Sakai, Yukio Furukawa, Norihiro Tokitoh. Synthesis of a stable 1,2-bis(ferrocenyl)diphosphene. Chemical Communications 2012, 48 (68) , 8562. https://doi.org/10.1039/c2cc33277a

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