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A Chemical Trick:  How To Make a Digermene from a Disilene, Formation of 3Δ-1,2,3,4-Disiladigermetene

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Department of Chemistry, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
Cite this: J. Am. Chem. Soc. 2003, 125, 20, 6012–6013
Publication Date (Web):April 19, 2003
https://doi.org/10.1021/ja021480s
Copyright © 2003 American Chemical Society
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Abstract

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The unexpected reaction of tetrakis[di-tert-butyl(methyl)silyl]disilagermirenes (1a and 1b) with GeCl2·dioxane results in the quantitative formation of trans-1,2-dichloro-1,2,3,4-tetrakis[di-tert-butyl(methyl)silyl]-3Δ-1,2,3,4-disiladigermetene, 2, representing the first cyclotetrametallene containing two different heavier group 14 elements and the first digermene incorporated in a four-membered ring. trans-1,2-Dichloro-1,2,3,4-tetrakis[di-tert-butyl(methyl)silyl]-3Δ-1,2,3,4-disilagermastannetene (8), with a GeSn double bond, was also prepared by the reaction of 1 with SnCl2·dioxane. The crystal structure of 2 was established by X-ray crystallography, which showed a folded four-membered ring skeleton with a long GeGe double bond (2.2911(4) Å). The structural peculiarities of 2, as well as the possible mechanism of its formation, are also discussed.

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Experimental procedures and spectral data of 2 and 8, tables of crystallographic data including atomic positional and thermal parameters for 2 (PDF). This material is available free of charge via the Internet at http://pubs.acs.org.

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  12. Yan Wang, Xiaolan Zeng. Addition Reactions of H2O to Germastannenes: A Computational Study. Russian Journal of Physical Chemistry A 2018, 92 (9) , 1699-1705. https://doi.org/10.1134/S0036024418090352
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  15. Carsten Präsang, David Scheschkewitz. Reactivity in the periphery of functionalised multiple bonds of heavier group 14 elements. Chemical Society Reviews 2016, 45 (4) , 900-921. https://doi.org/10.1039/C5CS00720H
  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. Christoph Marschner. Oligosilanes. 2013,,, 163-228. https://doi.org/10.1007/430_2013_103
  18. . Functional Molecular Silicon Compounds I. 2014,,https://doi.org/10.1007/978-3-319-03620-5
  19. V.Ya. Lee, A. Sekiguchi. Multiply Bonded Compounds of Group 14 Elements. 2013,,, 289-324. https://doi.org/10.1016/B978-0-08-097774-4.00113-3
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  23. Vladimir Ya. Lee, Yuki Ito, Akira Sekiguchi. 1,2-Dibromo- 3 Δ-1,2,3,4-disiladigermetene. Phosphorus, Sulfur, and Silicon and the Related Elements 2011, 186 (6) , 1351-1355. https://doi.org/10.1080/10426507.2010.543104
  24. . Heavy Analogs of Alkenes, 1,3-Dienes, Allenes and Alkynes: Multiply Bonded Derivatives of Si, Ge, Sn and Pb. 2010,,, 199-334. https://doi.org/10.1002/9780470669266.ch5
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  29. Mark M. Banaszak Holl, David R. Peck. Germanimum: Organometallic Chemistry. 2009,,https://doi.org/10.1002/0470862106.ia080.pub2
  30. , , , , . Encyclopedia of Inorganic Chemistry. 2006,,https://doi.org/
  31. Yuji Naruse, Satoshi Inagaki. Relaxation of Ring Strains. 2009,,, 265-291. https://doi.org/10.1007/128_2008_42
  32. . Orbitals in Chemistry. 2010,,https://doi.org/10.1007/978-3-642-01751-3
  33. Vladimir Ya. Lee, Akira Sekiguchi. Cyclic polyenes of heavy group 14 elements: new generation ligands for transition-metal complexes. Chemical Society Reviews 2008, 37 (8) , 1652. https://doi.org/10.1039/b800580j
  34. Vladimir Ya. Lee, Akira Sekiguchi. Aromatizität von metallorganischen Verbindungen mit Gruppe-14-Elementen: experimentelle Aspekte. Angewandte Chemie 2007, 119 (35) , 6716-6740. https://doi.org/10.1002/ange.200604869
  35. Vladimir Ya. Lee, Akira Sekiguchi. Aromaticity of Group 14 Organometallics: Experimental Aspects. Angewandte Chemie International Edition 2007, 46 (35) , 6596-6620. https://doi.org/10.1002/anie.200604869
  36. Vladimir Ya. Lee, Kazunori Takanashi, Risa Kato, Tadahiro Matsuno, Masaaki Ichinohe, Akira Sekiguchi. Heavy analogues of the 6π-electron anionic ring systems: Cyclopentadienide ion and cyclobutadiene dianion. Journal of Organometallic Chemistry 2007, 692 (13) , 2800-2810. https://doi.org/10.1016/j.jorganchem.2007.01.011
  37. Vladimir Ya. Lee, Hiroyuki Yasuda, Masaaki Ichinohe, Akira Sekiguchi. Heavy cyclopropene analogues R4SiGe2 and R4Ge3 (R=SiMetBu2) – New members of the cyclic digermenes family. Journal of Organometallic Chemistry 2007, 692 (1-3) , 10-19. https://doi.org/10.1016/j.jorganchem.2006.03.049
  38. Mitsuo Kira, Takeaki Iwamoto. Progress in the Chemistry of Stable Disilenes. 2006,,, 73-148. https://doi.org/10.1016/S0065-3055(05)54003-6
  39. . . 2006,,https://doi.org/
  40. Benito Alcaide, Pedro Almendros. Chapter 4 Four-membered ring systems. 2005,,, 82-97. https://doi.org/10.1016/S0959-6380(05)80046-7
  41. . A critical review of the 2003 literature preceded by two chapters on current heterocyclic topics. 2005,,https://doi.org/
  42. Vladimir Ya. Lee, Kazunori Takanashi, Masaaki Ichinohe, Akira Sekiguchi. The First Bicyclo[1.1.0]butane Dianion of Heavier Group 14 Elements. Angewandte Chemie 2004, 116 (48) , 6871-6873. https://doi.org/10.1002/ange.200461602
  43. Vladimir Ya. Lee, Kazunori Takanashi, Masaaki Ichinohe, Akira Sekiguchi. The First Bicyclo[1.1.0]butane Dianion of Heavier Group 14 Elements. Angewandte Chemie International Edition 2004, 43 (48) , 6703-6705. https://doi.org/10.1002/anie.200461602

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