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Isolable Anion Radical of Blue Disilene (tBu2MeSi)2SiSi(SiMetBu2)2 Formed upon One-Electron Reduction:  Synthesis and Characterization

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Contribution from the Department of Chemistry, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
Cite this: J. Am. Chem. Soc. 2004, 126, 31, 9626–9629
Publication Date (Web):July 17, 2004
https://doi.org/10.1021/ja040079y
Copyright © 2004 American Chemical Society
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Abstract

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The highly twisted tetrakis(di-tert-butylmethylsilyl)disilene 4 was prepared and reacted with tBuLi in THF, producing disilene anion radical 5 upon one-electron reduction. The anion radical 5 was isolated in the form of its lithium salt as extremely air- and moisture-sensitive red crystals. The molecular structure of 5 was established by X-ray crystallography, which showed a nearly orthogonal structure (twisting angle of 88°) along the central Si−Si bond, with a length of 2.341(5) Å, which is 3.6% elongated relative to that of 4. The interesting feature of 5 is that one of the central Si atoms has radical character, whereas the other Si atom has silyl anion character. An electron spin resonance (ESR) study of the hyperfine coupling constants of the 29Si nuclei indicates that rapid spin exchange occurs between these central Si atoms on the ESR time scale.

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Tables of crystallographic data including atomic positional and thermal parameters for 4 and 5. This material is available free of charge via the Internet at http://pubs.acs.org.

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  2. Prasenjit Bag, Amelie Porzelt, Philipp J. Altmann, and Shigeyoshi Inoue . A Stable Neutral Compound with an Aluminum–Aluminum Double Bond. Journal of the American Chemical Society 2017, 139 (41) , 14384-14387. https://doi.org/10.1021/jacs.7b08890
  3. Daniel Wendel, Tibor Szilvási, Christian Jandl, Shigeyoshi Inoue, and Bernhard Rieger . Twist of a Silicon–Silicon Double Bond: Selective Anti-Addition of Hydrogen to an Iminodisilene. Journal of the American Chemical Society 2017, 139 (27) , 9156-9159. https://doi.org/10.1021/jacs.7b05335
  4. Shu-Hua Zhang, Emma Carter, Hong-Wei Xi, Yongxin Li, Kok Hwa Lim, and Cheuk-Wai So . Delocalized Hypervalent Silyl Radical Supported by Amidinate and Imino Substituents. Inorganic Chemistry 2017, 56 (2) , 701-704. https://doi.org/10.1021/acs.inorgchem.6b02427
  5. Zhendong Wang, Jianying Zhang, Jianfeng Li, and Chunming Cui . NHC-Stabilized Silicon–Carbon Mixed Cumulene. Journal of the American Chemical Society 2016, 138 (33) , 10421-10424. https://doi.org/10.1021/jacs.6b06960
  6. Akihiro Tsurusaki, Chisato Iizuka, Kyohei Otsuka, and Soichiro Kyushin . Cyclopentasilane-Fused Hexasilabenzvalene. Journal of the American Chemical Society 2013, 135 (44) , 16340-16343. https://doi.org/10.1021/ja409074m
  7. Lieby Zborovsky, Roman Dobrovetsky, Mark Botoshansky, Dmitry Bravo-Zhivotovskii, and Yitzhak Apeloig . Synthesis of Silenyllithiums Li(R′3Si)Si═C(SiR3)(1-Ad) via Transient Silyne–Silylidene Intermediates. Journal of the American Chemical Society 2012, 134 (44) , 18229-18232. https://doi.org/10.1021/ja308777v
  8. Mitsuo Kira . Distortion Modes of Heavy Ethylenes and Their Anions: π–σ* Orbital Mixing Model. Organometallics 2011, 30 (16) , 4459-4465. https://doi.org/10.1021/om200609d
  9. Jonathan Jeck, Iulia Bejan, Andrew J. P. White, Dominik Nied, Frank Breher, and David Scheschkewitz . Transfer of a Disilenyl Moiety to Aromatic Substrates and Lateral Functional Group Transformation in Aryl Disilenes. Journal of the American Chemical Society 2010, 132 (48) , 17306-17315. https://doi.org/10.1021/ja107547s
  10. Roland C. Fischer and Philip P. Power . π-Bonding and the Lone Pair Effect in Multiple Bonds Involving Heavier Main Group Elements: Developments in the New Millennium. Chemical Reviews 2010, 110 (7) , 3877-3923. https://doi.org/10.1021/cr100133q
  11. Takeaki Iwamoto, Yuichi Furiya, Hideki Kobayashi, Hiroyuki Isobe and Mitsuo Kira. Synthesis and Facile Ring Expansion of Silylenecyclotetrasilane. Organometallics 2010, 29 (8) , 1869-1872. https://doi.org/10.1021/om9010577
  12. Hiroaki Tanaka, Shigeyoshi Inoue, Masaaki Ichinohe and Akira Sekiguchi. An (η3-Disilaallyl)lithium Derivative: Interconversion of π-Allyl-Type Bonding and η1 Coordination to a Silyllithium Fragment. Organometallics 2009, 28 (23) , 6625-6628. https://doi.org/10.1021/om900861z
  13. Gregory Molev, Boris Tumanskii, Dennis Sheberla, Mark Botoshansky, Dmitry Bravo-Zhivotovskii and Yitzhak Apeloig. Isolable Photoreactive Polysilyl Radicals. Journal of the American Chemical Society 2009, 131 (33) , 11698-11700. https://doi.org/10.1021/ja905097b
  14. 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
  15. Michaela Zirngast, Michaela Flock, Judith Baumgartner and Christoph Marschner. Formation of Formal Disilene Fluoride Adducts. Journal of the American Chemical Society 2008, 130 (51) , 17460-17470. https://doi.org/10.1021/ja805753d
  16. Shigeyoshi Inoue, Masaaki Ichinohe, Torahiko Yamaguchi and Akira Sekiguchi. A Free Silylium Ion: A Cyclotetrasilenylium Ion with Allylic Character. Organometallics 2008, 27 (23) , 6056-6058. https://doi.org/10.1021/om800912v
  17. Shigeyoshi Inoue, Masaaki Ichinohe and Akira Sekiguchi. The Isolable Cation Radical of Disilene: Synthesis, Characterization, and a Reversible One-Electron Redox System. Journal of the American Chemical Society 2008, 130 (19) , 6078-6079. https://doi.org/10.1021/ja801761w
  18. Shigeyoshi Inoue, Masaaki Ichinohe and Akira Sekiguchi. Isolable Alkali-Metal-Substituted Silyl Radicals (tBu2MeSi)2SiM (M = Li, Na, K): Electronically and Sterically Accessible Planar Silyl Radicals. Organometallics 2008, 27 (7) , 1358-1360. https://doi.org/10.1021/om8000185
  19. Takeshi Matsumoto, Takahiro Sasamori, Kazunobu Sato, Takeji Takui and Norihiro Tokitoh. Reduction of a Kinetically Stabilized Silabenzene Leading to the Formation of the Corresponding Anion Radical Species. Organometallics 2008, 27 (3) , 305-308. https://doi.org/10.1021/om701060a
  20. Aiko Fukazawa,, Yongming Li,, Shigehiro Yamaguchi,, Hayato Tsuji, and, Kohei Tamao. Coplanar Oligo(p-phenylenedisilenylene)s Based on the Octaethyl-Substituted s-Hydrindacenyl Groups. Journal of the American Chemical Society 2007, 129 (46) , 14164-14165. https://doi.org/10.1021/ja0764207
  21. Vladimir Ya. Lee and Akira Sekiguchi. Stable Silyl, Germyl, and Stannyl Cations, Radicals, and Anions: Heavy Versions of Carbocations, Carbon Radicals, and Carbanions. Accounts of Chemical Research 2007, 40 (6) , 410-419. https://doi.org/10.1021/ar6000473
  22. Vladimir Ya. Lee,, Hiroyuki Yasuda, and, Akira Sekiguchi. Interplay of EnE‘3-nC Valence Isomers (E, E‘ = Si, Ge):  Bicyclo[1.1.0]butanes with Very Short Bridging Bonds and Their Isomerization to Alkyl-Substituted Cyclopropenes. Journal of the American Chemical Society 2007, 129 (9) , 2436-2437. https://doi.org/10.1021/ja068229n
  23. Vladimir Ya. Lee,, Tomohide Fukawa,, Masaaki Nakamoto,, Akira Sekiguchi,, Boris L. Tumanskii,, Miriam Karni, and, Yitzhak Apeloig. (tBu2MeSi)2SnSn(SiMetBu2)2:  A Distannene with a >SnSn< Double Bond That Is Stable Both in the Solid State and in Solution. Journal of the American Chemical Society 2006, 128 (35) , 11643-11651. https://doi.org/10.1021/ja063322x
  24. Thi-loan Nguyen and, David Scheschkewitz. Activation of a SiSi Bond by η-Coordination to a Transition Metal. Journal of the American Chemical Society 2005, 127 (29) , 10174-10175. https://doi.org/10.1021/ja052593p
  25. Masae Takahashi and, Yoshiyuki Kawazoe. Theoretical Study on Planar Anionic Polysilicon Chains and Cyclic Si6 Anions with D6h Symmetry. Organometallics 2005, 24 (10) , 2433-2440. https://doi.org/10.1021/om050025c
  26. Franziska Hanusch, Lisa Groll, Shigeyoshi Inoue. Recent advances of group 14 dimetallenes and dimetallynes in bond activation and catalysis. Chemical Science 2021, 79 https://doi.org/10.1039/D0SC03192E
  27. Shintaro Takahashi, Kazuki Nakaya, María Frutos, Antoine Baceiredo, Nathalie Saffon‐Merceron, Stéphane Massou, Norio Nakata, Daisuke Hashizume, Vicenç Branchadell, Tsuyoshi Kato. Synthesis of a Stable N‐Hetero ‐ Rh I ‐Metallacyclic Silanone. Angewandte Chemie 2020, 132 (37) , 16071-16075. https://doi.org/10.1002/ange.202006088
  28. Shintaro Takahashi, Kazuki Nakaya, María Frutos, Antoine Baceiredo, Nathalie Saffon‐Merceron, Stéphane Massou, Norio Nakata, Daisuke Hashizume, Vicenç Branchadell, Tsuyoshi Kato. Synthesis of a Stable N‐Hetero ‐ Rh I ‐Metallacyclic Silanone. Angewandte Chemie International Edition 2020, 59 (37) , 15937-15941. https://doi.org/10.1002/anie.202006088
  29. Richard Holzner, Dominik Reiter, Philipp Frisch, Shigeyoshi Inoue. DMAP-stabilized bis(silyl)silylenes as versatile synthons for organosilicon compounds. RSC Advances 2020, 10 (6) , 3402-3406. https://doi.org/10.1039/C9RA10628F
  30. 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
  31. Philipp Frisch, Shigeyoshi Inoue. NHC-stabilized silyl-substituted silyliumylidene ions. Dalton Transactions 2019, 48 (28) , 10403-10406. https://doi.org/10.1039/C9DT02010A
  32. Richard Holzner, Alexander Kaushansky, Boris Tumanskii, Philipp Frisch, Fabian Linsenmann, Shigeyoshi Inoue. Isolation of a Relatively Air-Stable, Bulky Silyl-Substituted, Neutral Silicon-Centered Radical. European Journal of Inorganic Chemistry 2019, 2019 (25) , 2977-2981. https://doi.org/10.1002/ejic.201900522
  33. Takeaki Iwamoto, Takashi Abe, Kunihisa Sugimoto, Daisuke Hashizume, Hiroshi Matsui, Ryohei Kishi, Masayoshi Nakano, Shintaro Ishida. A Tetrasilicon Analogue of Bicyclo[1.1.0]but‐1(3)‐ene Containing a Si=Si Double Bond with an Inverted Geometry. Angewandte Chemie 2019, 131 (13) , 4415-4419. https://doi.org/10.1002/ange.201900824
  34. Takeaki Iwamoto, Takashi Abe, Kunihisa Sugimoto, Daisuke Hashizume, Hiroshi Matsui, Ryohei Kishi, Masayoshi Nakano, Shintaro Ishida. A Tetrasilicon Analogue of Bicyclo[1.1.0]but‐1(3)‐ene Containing a Si=Si Double Bond with an Inverted Geometry. Angewandte Chemie International Edition 2019, 58 (13) , 4371-4375. https://doi.org/10.1002/anie.201900824
  35. Julian Böhnke, Theresa Dellermann, Mehmet Ali Celik, Ivo Krummenacher, Rian D. Dewhurst, Serhiy Demeshko, William C. Ewing, Kai Hammond, Merlin Heß, Eckhard Bill, Eileen Welz, Merle I. S. Röhr, Roland Mitrić, Bernd Engels, Franc Meyer, Holger Braunschweig. Isolation of diborenes and their 90°-twisted diradical congeners. Nature Communications 2018, 9 (1) https://doi.org/10.1038/s41467-018-02998-3
  36. Vitaly Nesterov, Nora C. Breit, Shigeyoshi Inoue. Advances in Phosphasilene Chemistry. Chemistry - A European Journal 2017, 23 (50) , 12014-12039. https://doi.org/10.1002/chem.201700829
  37. Soichiro Kyushin. Organosilicon Clusters. 2017,,, 69-144. https://doi.org/10.1016/B978-0-12-801981-8.00003-4
  38. . Organosilicon Compounds. 2017,,https://doi.org/
  39. Boris Tumanskii, Miriam Karni, Yitzhak Apeloig. Silicon-Centered Radicals. 2017,,, 231-294. https://doi.org/10.1016/B978-0-12-801981-8.00006-X
  40. . Organosilicon Compounds. 2017,,https://doi.org/
  41. Takeaki Iwamoto, Shintaro Ishida. Stable Silylenes and Their Transition Metal Complexes. 2017,,, 361-532. https://doi.org/10.1016/B978-0-12-801981-8.00008-3
  42. . Organosilicon Compounds. 2017,,https://doi.org/
  43. Antoine Baceiredo, Tsuyoshi Kato. Multiple Bonds to Silicon (Recent Advances in the Chemistry of Silicon Containing Multiple Bonds). 2017,,, 533-618. https://doi.org/10.1016/B978-0-12-801981-8.00009-5
  44. . Organosilicon Compounds. 2017,,https://doi.org/
  45. Benedikt Niepötter, Dietmar Stalke. X-Ray Crystallography of Organosilicon Compounds (Electron Density and Chemical Bonding in Organosilicon Compounds). 2017,,, 3-58. https://doi.org/10.1016/B978-0-12-814213-4.00001-0
  46. . Organosilicon Compounds. 2017,,https://doi.org/
  47. Frank Uhlig. 29 Si NMR Spectroscopy. 2017,,, 59-77. https://doi.org/10.1016/B978-0-12-814213-4.00002-2
  48. . Organosilicon Compounds. 2017,,https://doi.org/
  49. Akihiro Tsurusaki, Soichiro Kyushin. The Radical Anion of Cyclopentasilane‐Fused Hexasilabenzvalene. Chemistry – A European Journal 2016, 22 (1) , 134-137. https://doi.org/10.1002/chem.201504449
  50. 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
  51. . Efficient Methods for Preparing Silicon Compounds. 2016,,https://doi.org/
  52. S.U. Ahmad, S. Inoue. Multiple Bonding in Silicon Compounds. 2016,,, 73-89. https://doi.org/10.1016/B978-0-12-803530-6.00007-X
  53. . Efficient Methods for Preparing Silicon Compounds. 2016,,https://doi.org/
  54. Kartik Chandra Mondal, Sudipta Roy, Herbert W. Roesky. Silicon based radicals, radical ions, diradicals and diradicaloids. Chemical Society Reviews 2016, 45 (4) , 1080-1111. https://doi.org/10.1039/C5CS00739A
  55. Vladimir Ya. Lee, Akira Sekiguchi. Heavier Group 14 Element Redox Systems. 2015,,, 545-561. https://doi.org/10.1002/9781118858981.ch19
  56. . Organic Redox Systems. 2016,,https://doi.org/10.1002/9781118858981
  57. Arseni Kostenko, Boris Tumanskii, Miriam Karni, Shigeyoshi Inoue, Masaaki Ichinohe, Akira Sekiguchi, Yitzhak Apeloig. Observation of a Thermally Accessible Triplet State Resulting from Rotation around a Main-Group π Bond. Angewandte Chemie 2015, 127 (41) , 12312-12316. https://doi.org/10.1002/ange.201506291
  58. Arseni Kostenko, Boris Tumanskii, Miriam Karni, Shigeyoshi Inoue, Masaaki Ichinohe, Akira Sekiguchi, Yitzhak Apeloig. Observation of a Thermally Accessible Triplet State Resulting from Rotation around a Main-Group π Bond. Angewandte Chemie International Edition 2015, 54 (41) , 12144-12148. https://doi.org/10.1002/anie.201506291
  59. Marius I. Arz, Martin Straßmann, Andreas Meyer, Gregor Schnakenburg, Olav Schiemann, Alexander C. Filippou. One-Electron Oxidation of a Disilicon(0) Compound: An Experimental and Theoretical Study of [Si 2 ] + Trapped by N-Heterocyclic Carbenes. Chemistry - A European Journal 2015, 21 (35) , 12509-12516. https://doi.org/10.1002/chem.201502199
  60. 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
  61. 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
  62. Soichiro Kyushin, Shintaro Ishida, Akihiro Tsurusaki, Kyohei Otsuka. Effect of Ring Sizes of Cyclooligosilanes on Construction of Organosilicon Clusters. Journal of Synthetic Organic Chemistry, Japan 2014, 72 (11) , 1290-1297. https://doi.org/10.5059/yukigoseikyokaishi.72.1290
  63. Carsten Präsang, David Scheschkewitz. Silyl Anions. 2013,,, 1-47. https://doi.org/10.1007/430_2013_104
  64. . Functional Molecular Silicon Compounds II. 2014,,https://doi.org/10.1007/978-3-319-03734-9
  65. Takeaki Iwamoto, Shintaro Ishida. Multiple Bonds with Silicon: Recent Advances in Synthesis, Structure, and Functions of Stable Disilenes. 2013,,, 125-202. https://doi.org/10.1007/430_2013_119
  66. . Functional Molecular Silicon Compounds II. 2014,,https://doi.org/10.1007/978-3-319-03734-9
  67. 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
  68. . Comprehensive Inorganic Chemistry II. 2013,,https://doi.org/
  69. T. Chivers, J. Konu. Stable and Persistent Radicals of Group 13-17 Elements. 2013,,, 349-373. https://doi.org/10.1016/B978-0-08-097774-4.00116-9
  70. . Comprehensive Inorganic Chemistry II. 2013,,https://doi.org/
  71. Caleb D. Martin, Michele Soleilhavoup, Guy Bertrand. Carbene-stabilized main group radicals and radical ions. Chemical Science 2013, 4 (8) , 3020. https://doi.org/10.1039/c3sc51174j
  72. Boris Tumanskii, Miriam Karni, Yitzhak Apeloig. Persistent and Stable Silyl Radicals. 2012,,https://doi.org/10.1002/9781119953678.rad066
  73. , . Encyclopedia of Radicals in Chemistry, Biology and Materials. 2012,,https://doi.org/
  74. Mitsuo KIRA. Bonding and structure of disilenes and related unsaturated group-14 element compounds. Proceedings of the Japan Academy, Series B 2012, 88 (5) , 167-191. https://doi.org/10.2183/pjab.88.167
  75. Vitaly G. Avakyan, Evgeniya P. Doronina, Stephan L. Guselnikov, Valery F. Sidorkin. Ditopic complexes of silene H2SiCH2 with bidentate ligands Me2NCH2SiHnF3-n. Structures, formation energies, AIM and ELF analyses.. Journal of Organometallic Chemistry 2011, 696 (10) , 1969-1974. https://doi.org/10.1016/j.jorganchem.2010.10.032
  76. David Scheschkewitz. The Versatile Chemistry of Disilenides: Disila Analogues of Vinyl Anions as Synthons in Low-valent Silicon Chemistry. Chemistry Letters 2011, 40 (1) , 2-11. https://doi.org/10.1246/cl.2011.2
  77. Vladimir Ya. Lee, Kiera McNeice, Yuki Ito, Akira Sekiguchi. A blue digermene (t-Bu2MeSi)2GeGe(SiMet-Bu2)2. Chemical Communications 2011, 47 (11) , 3272. https://doi.org/10.1039/c0cc05415a
  78. Takeaki Iwamoto, Junichiro Okita, Naoki Yoshida, Mitsuo Kira. Structure and Reactions of an Isolable Ge=Si Doubly Bonded Compound, Tetra(t-butyldimethylsilyl)germasilene. Silicon 2010, 2 (4) , 209-216. https://doi.org/10.1007/s12633-011-9069-8
  79. . Heavy Analogs of Organic Free Radicals: Si-, Ge-, Sn- and Pb-Centered Radicals. 2010,,, 45-88. https://doi.org/10.1002/9780470669266.ch2
  80. Vladimir Ya. Lee, Akira Sekiguchi. Organometallic Compounds of Low-Coordinate Si, Ge, Sn and Pb. 2010,,https://doi.org/
  81. . 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
  82. Vladimir Ya. Lee, Akira Sekiguchi. Organometallic Compounds of Low-Coordinate Si, Ge, Sn and Pb. 2010,,https://doi.org/
  83. Jari Konu, Tristram Chivers. Stable Radicals of the Heavy p-Block Elements. 2010,,, 381-406. https://doi.org/10.1002/9780470666975.ch10
  84. . Stable Radicals. 2010,,https://doi.org/10.1002/9780470666975
  85. Tsukasa Matsuo, Megumi Kobayashi, Kohei Tamao. π-Conjugated disilenes stabilized by fused-ring bulky “Rind” groups. Dalton Transactions 2010, 39 (39) , 9203. https://doi.org/10.1039/c0dt00287a
  86. Sakya S. Sen, Anukul Jana, Herbert W. Roesky, Carola Schulzke. A Remarkable Base-Stabilized Bis(silylene) with a Silicon(I)-Silicon(I) Bond. Angewandte Chemie 2009, 121 (45) , 8688-8690. https://doi.org/10.1002/ange.200902995
  87. Sakya S. Sen, Anukul Jana, Herbert W. Roesky, Carola Schulzke. A Remarkable Base-Stabilized Bis(silylene) with a Silicon(I)-Silicon(I) Bond. Angewandte Chemie International Edition 2009, 48 (45) , 8536-8538. https://doi.org/10.1002/anie.200902995
  88. Annemarie Schäfer, Manfred Weidenbruch, Thomas Müller, Kendrekar Pravinkumar, James Y. Becker. Electrochemical Properties of a Disilene, a Tetrasila-1,3-butadiene, and Their Germanium Analogues. Chemistry - A European Journal 2009, 15 (34) , 8424-8428. https://doi.org/10.1002/chem.200901001
  89. David Scheschkewitz. Anionic Reagents with Silicon-Containing Double Bonds. Chemistry - A European Journal 2009, 15 (11) , 2476-2485. https://doi.org/10.1002/chem.200801968
  90. 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
  91. . Electronic Structure–Reactivity Relationship in Ion-Radical Organic Chemistry. 2008,,, 143-203. https://doi.org/10.1201/9781420008395.ch3
  92. Zory Vlad Todres. Ion-Radical Organic Chemistry. 2008,,https://doi.org/10.1201/9781420008395
  93. Shigeyoshi Inoue, Masaaki Ichinohe, Akira Sekiguchi. An Isolable Boryl-substituted Disilene from the Reaction of an sp 2 -type Silyl Anion with Haloboranes: Synthesis and Characterization. Chemistry Letters 2008, 37 (10) , 1044-1045. https://doi.org/10.1246/cl.2008.1044
  94. Karl Hassler, Ana Dzambaski, Judith Baumgartner. Dihaloheptasilanes X2Si[SiMe(SiMe3)2]2 as potential precursors for silylenes, disilenes and cyclotrisilanes. Silicon Chemistry 2008, 3 (6) , 271-288. https://doi.org/10.1007/s11201-007-9029-8
  95. Vladimir Ya. Lee, Masaaki Nakamoto, Akira Sekiguchi. Making Stable Radicals of Heavy Elements of Groups 14 and 13: The Might of Silyl Substitution. Chemistry Letters 2008, 37 (2) , 128-133. https://doi.org/10.1246/cl.2008.128
  96. Iulia Bejan, David Scheschkewitz. Phenylenverbrückung zwischen zwei Si-Si-Doppelbindungen. Angewandte Chemie 2007, 119 (30) , 5885-5888. https://doi.org/10.1002/ange.200701744
  97. Iulia Bejan, David Scheschkewitz. Two SiSi Double Bonds Connected by a Phenylene Bridge. Angewandte Chemie International Edition 2007, 46 (30) , 5783-5786. https://doi.org/10.1002/anie.200701744
  98. 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
  99. Shigeyoshi Inoue, Masaaki Ichinohe, Akira Sekiguchi. Conversion of a Disilenide into a Silene: Silyl-Anion-Substituted Silene by a Sila-Peterson-Type Reaction from an sp2-Type Silyl Anion. Angewandte Chemie 2007, 119 (18) , 3410-3412. https://doi.org/10.1002/ange.200605140
  100. Shigeyoshi Inoue, Masaaki Ichinohe, Akira Sekiguchi. Conversion of a Disilenide into a Silene: Silyl-Anion-Substituted Silene by a Sila-Peterson-Type Reaction from an sp2-Type Silyl Anion. Angewandte Chemie International Edition 2007, 46 (18) , 3346-3348. https://doi.org/10.1002/anie.200605140

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