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Reactivity of an Aryl-Substituted Silicon−Silicon Triple Bond: Reactions of a 1,2-Diaryldisilyne with Alkenes

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Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan
Cite this: J. Am. Chem. Soc. 2010, 132, 8, 2546–2547
Publication Date (Web):February 3, 2010
https://doi.org/10.1021/ja9108566
Copyright © 2010 American Chemical Society
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Abstract

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The reactivity of a bulky, diaryl-substituted disilyne, Ar−Si≡Si−Ar, was examined for the first time. Reaction of the disilyne with ethylene yielded an ethylene-bridged bis(silacyclopropane), which is interpreted as a further reaction product of the initially formed 1,2-disilacyclobutene species with ethylene. A cyclohexane fused with a 1,2-disilacyclobutene was obtained in the reaction with cyclohexene. In the reaction with 2,3-dimethyl-1,3-butadiene, a tricyclo derivative was isolated from the complex product mixture.

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Experimental details, characterization data for new compounds, and crystallographic data for 2, 3, and 4 (CIF). This material is available free of charge via the Internet at http://pubs.acs.org.

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  1. Yuwen Wang, Miriam Karni, Shenglai Yao, Alexander Kaushansky, Yitzhak Apeloig, Matthias Driess. Synthesis of an Isolable Bis(silylene)-Stabilized Silylone and Its Reactivity Toward Small Gaseous Molecules. Journal of the American Chemical Society 2019, 141 (32) , 12916-12927. https://doi.org/10.1021/jacs.9b06603
  2. Kelly L. Gullett, Ting Yi Lai, Chia-Yuan Chen, James C. Fettinger, Philip P. Power. Reversible Binding of Ethylene and Propylene by Germylenes. Organometallics 2019, 38 (7) , 1425-1428. https://doi.org/10.1021/acs.organomet.9b00109
  3. Madison L. McCrea-Hendrick, Christine A. Caputo, Jarno Linnera, Petra Vasko, Cory M. Weinstein, James C. Fettinger, Heikki M. Tuononen, and Philip P. Power . Cleavage of Ge–Ge and Sn–Sn Triple Bonds in Heavy Group 14 Element Alkyne Analogues (EAriPr4)2 (E = Ge, Sn; AriPr4 = C6H3-2,6(C6H3-2,6-iPr2)2) by Reaction with Group 6 Carbonyls. Organometallics 2016, 35 (16) , 2759-2767. https://doi.org/10.1021/acs.organomet.6b00519
  4. Miroslav Novák, Marek Bouška, Libor Dostál, Aleš Růžička, and Roman Jambor . Intramolecularly C,N-Coordinated Homo- and Heteroleptic Organostannylenes. Organometallics 2014, 33 (23) , 6778-6784. https://doi.org/10.1021/om500698k
  5. Felicitas Lips, James C. Fettinger, Akseli Mansikkamäki, Heikki M. Tuononen, and Philip P. Power . Reversible Complexation of Ethylene by a Silylene under Ambient Conditions. Journal of the American Chemical Society 2014, 136 (2) , 634-637. https://doi.org/10.1021/ja411951y
  6. Michael Wagner, Christina Dietz, Stefan Krabbe, Stephan G. Koller, Carsten Strohmann, and Klaus Jurkschat . {4-t-Bu-2,6-[P(O)(O-i-Pr)2]2C6H2Sn}2: An Intramolecularly Coordinated Organotin(I) Compound with a Sn–Sn Single Bond, Its Disproportionation toward a Diorganostannylene and Elemental Tin, and Its Oxidation with PhI(OAc)2. Inorganic Chemistry 2012, 51 (12) , 6851-6859. https://doi.org/10.1021/ic3005954
  7. LiLi Zhao, Fang Huang, Gang Lu, Zhi-Xiang Wang, and Paul von Ragué Schleyer . Why the Mechanisms of Digermyne and Distannyne Reactions with H2 Differ So Greatly. Journal of the American Chemical Society 2012, 134 (21) , 8856-8868. https://doi.org/10.1021/ja300111q
  8. Katsuhiko Takeuchi, Masaaki Ichinohe, and Akira Sekiguchi . A New Disilene with π-Accepting Groups from the Reaction of Disilyne RSi≡SiR (R = SiiPr[CH(SiMe3)2]) with Isocyanides. Journal of the American Chemical Society 2012, 134 (6) , 2954-2957. https://doi.org/10.1021/ja212065a
  9. Katsuhiko Takeuchi, Masaaki Ichinohe, and Akira Sekiguchi . Access to a Stable Si2N2 Four-Membered Ring with Non-Kekulé Singlet Biradical Character from a Disilyne. Journal of the American Chemical Society 2011, 133 (32) , 12478-12481. https://doi.org/10.1021/ja2059846
  10. Torahiko Yamaguchi and Akira Sekiguchi . Unusual Reactivity of a Disilyne with 4-Dimethylaminopyridine: Formation of an Intramolecularly N-Coordinated Silylene and Its Isomerization to a Zwitterionic Silyl Anion. Journal of the American Chemical Society 2011, 133 (19) , 7352-7354. https://doi.org/10.1021/ja202605x
  11. Katsuhiko Takeuchi, Masaaki Ichinohe, and Akira Sekiguchi . Hydroboration of Disilyne RSi≡SiR (R = SiiPr[CH(SiMe3)2]2), Giving Boryl-Substituted Disilenes. Organometallics 2011, 30 (7) , 2044-2050. https://doi.org/10.1021/om200106h
  12. Ganesh Chandra Nandi. Advances in the Synthesis and Applications of Three Membered Sila, Sila‐Aza/‐Phospha/‐Oxa/‐Thia Cyclopropanes. European Journal of Organic Chemistry 2021, 2021 (4) , 587-606. https://doi.org/10.1002/ejoc.202001123
  13. 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
  14. K. Yuvaraj, Iskander Douair, Laurent Maron, Cameron Jones. Activation of Ethylene by N‐Heterocyclic Carbene Coordinated Magnesium(I) Compounds. Chemistry – A European Journal 2020, 26 (64) , 14665-14670. https://doi.org/10.1002/chem.202002380
  15. Alexander Hinz. Synthesis and Thermal Decomposition of Heavy Tetrylenes Bearing N ‐Aminocarbazolyl Substituents. Chemistry – A European Journal 2019, 25 (33) , 7843-7846. https://doi.org/10.1002/chem.201901573
  16. Yunus E. Türkmen. Three-Membered Rings with One Silicon, Germanium, Tin or Lead Atom. 2019,,https://doi.org/10.1016/B978-0-12-409547-2.14787-0
  17. . Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. 2019,,https://doi.org/
  18. Jing-Dong Guo, Takahiro Sasamori. Activation of Small Molecules by Compounds that Contain Triple Bonds Between Heavier Group-14 Elements. Chemistry - An Asian Journal 2018, 13 (24) , 3800-3817. https://doi.org/10.1002/asia.201801329
  19. Alexander Hinz, Jose M. Goicoechea. Limitations of Steric Bulk: Towards Phospha‐germynes and Phospha‐stannynes. Chemistry – A European Journal 2018, 24 (29) , 7358-7363. https://doi.org/10.1002/chem.201801329
  20. Tomohiro Sugahara, Jing-Dong Guo, Takahiro Sasamori, Shigeru Nagase, Norihiro Tokitoh. Reversible addition of terminal alkenes to digermynes. Chemical Communications 2018, 54 (5) , 519-522. https://doi.org/10.1039/C7CC08555A
  21. Shintaro Ishida, Yoshifumi Misawa, Shohei Sugawara, Takeaki Iwamoto. Benzodisilacyclobutadienes: 8π-Electron Systems with an Antiaromatic Silicon Ring. Angewandte Chemie 2017, 129 (44) , 14017-14020. https://doi.org/10.1002/ange.201707553
  22. Shintaro Ishida, Yoshifumi Misawa, Shohei Sugawara, Takeaki Iwamoto. Benzodisilacyclobutadienes: 8π-Electron Systems with an Antiaromatic Silicon Ring. Angewandte Chemie International Edition 2017, 56 (44) , 13829-13832. https://doi.org/10.1002/anie.201707553
  23. Terrance John Hadlington. Synthesis and Reactivity of Heavier Alkyne Analogues Stabilised by Extremely Bulky Amide Ligands. 2017,,, 43-112. https://doi.org/10.1007/978-3-319-51807-7_3
  24. Terrance John Hadlington. On the Catalytic Efficacy of Low-Oxidation State Group 14 Complexes. 2017,,https://doi.org/10.1007/978-3-319-51807-7
  25. 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
  26. . Organosilicon Compounds. 2017,,https://doi.org/
  27. Tomohiro Sugahara, Jing-Dong Guo, Takahiro Sasamori, Yusaku Karatsu, Yukio Furukawa, Arturo Espinosa Ferao, Shigeru Nagase, Norihiro Tokitoh. Reaction of a Stable Digermyne with Acetylenes: Synthesis of a 1,2-Digermabenzene and a 1,4-Digermabarrelene. Bulletin of the Chemical Society of Japan 2016, 89 (11) , 1375-1384. https://doi.org/10.1246/bcsj.20160269
  28. Lili Zhao, Cameron Jones, Gernot Frenking. Reaction Mechanism of the Symmetry-Forbidden [2+2] Addition of Ethylene and Acetylene to Amido-Substituted Digermynes and Distannynes Ph 2 NEENPh 2 , (E=Ge, Sn): A Theoretical Study. Chemistry - A European Journal 2015, 21 (35) , 12405-12413. https://doi.org/10.1002/chem.201501457
  29. Miroslav Novák, Marek Bouška, Libor Dostál, Aleš Růžička, Alexander Hoffmann, Sonja Herres-Pawlis, Roman Jambor. Less Is More: Three-Coordinate C,N-Chelated Distannynes and Digermynes. Chemistry - A European Journal 2015, 21 (21) , 7820-7829. https://doi.org/10.1002/chem.201500695
  30. Takahiro Sasamori, Tomohiro Sugahara, Tomohiro Agou, Koh Sugamata, Jing-Dong Guo, Shigeru Nagase, Norihiro Tokitoh. Reaction of a diaryldigermyne with ethylene. Chemical Science 2015, 6 (10) , 5526-5530. https://doi.org/10.1039/C5SC01266J
  31. Di Wu, Rakesh Ganguly, Yongxin Li, Sin Ni Hoo, Hajime Hirao, Rei Kinjo. Reversible [4 + 2] cycloaddition reaction of 1,3,2,5-diazadiborinine with ethylene. Chemical Science 2015, 6 (12) , 7150-7155. https://doi.org/10.1039/C5SC03174E
  32. Marek Bouška, Miroslav Novák, Libor Dostál, Aleš Růžička, Tomáš Mikysek, Radovan Metelka, Roman Jambor. Oxidative Addition of Diorgano Disulfides to Distannyne [{2,6-(Me 2 NCH 2 ) 2 C 6 H 3 }Sn] 2. European Journal of Inorganic Chemistry 2014, 2014 (2) , 310-318. https://doi.org/10.1002/ejic.201300907
  33. 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
  34. Siew-Peng Chia, Hong-Wei Xi, Yongxin Li, Kok Hwa Lim, Cheuk-Wai So. A Base-Stabilized Lead(I) Dimer and an Aromatic Plumbylidenide Anion. Angewandte Chemie 2013, 125 (24) , 6418-6421. https://doi.org/10.1002/ange.201301954
  35. Siew-Peng Chia, Hong-Wei Xi, Yongxin Li, Kok Hwa Lim, Cheuk-Wai So. A Base-Stabilized Lead(I) Dimer and an Aromatic Plumbylidenide Anion. Angewandte Chemie International Edition 2013, 52 (24) , 6298-6301. https://doi.org/10.1002/anie.201301954
  36. 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
  37. . Functional Molecular Silicon Compounds II. 2014,,https://doi.org/10.1007/978-3-319-03734-9
  38. Matthew Asay, Akira Sekiguchi. Recent Developments in the Reactivity of Stable Disilynes. Bulletin of the Chemical Society of Japan 2012, 85 (12) , 1245-1261. https://doi.org/10.1246/bcsj.20120212
  39. Ricardo Rodriguez, David Gau, Tsuyoshi Kato, Nathalie Saffon-Merceron, Abel De Cózar, Fernando P. Cossío, Antoine Baceiredo. Reversible Binding of Ethylene to Silylene-Phosphine Complexes at Room Temperature. Angewandte Chemie 2011, 123 (44) , 10598-10600. https://doi.org/10.1002/ange.201105097
  40. Ricardo Rodriguez, David Gau, Tsuyoshi Kato, Nathalie Saffon-Merceron, Abel De Cózar, Fernando P. Cossío, Antoine Baceiredo. Reversible Binding of Ethylene to Silylene-Phosphine Complexes at Room Temperature. Angewandte Chemie International Edition 2011, 50 (44) , 10414-10416. https://doi.org/10.1002/anie.201105097
  41. Roland C. Fischer, Jan J. Weigand, Robert Wolf, Sven Rau, Ulrich Schatzschneider. Anorganische Chemie 2010. Nachrichten aus der Chemie 2011, 59 (3) , 221-245. https://doi.org/10.1002/nadc.201176368
  42. Marek Bouška, Libor Dostál, Aleš Růžička, Ludvík Beneš, Roman Jambor. Oxidation of Intramolecularly Coordinated Distannyne by S8: From Tin(I) to Tin(IV) Polysulfide Via Tin(II) Sulfide. Chemistry - A European Journal 2011, 17 (2) , 450-454. https://doi.org/10.1002/chem.201002584
  43. Marek Bouška, Libor Dostál, Frank de Proft, Aleš Růžička, Antonín Lyčka, Roman Jambor. Intramolecularly Coordinated Tin(II) Selenide and Triseleneoxostannonic Acid Anhydride. Chemistry - A European Journal 2011, 17 (2) , 455-459. https://doi.org/10.1002/chem.201002641
  44. Benito Alcaide, Pedro Almendros. Four-Membered Ring Systems. 2011,,, 101-125. https://doi.org/10.1016/B978-0-08-096805-6.00004-8
  45. . . 2011,,https://doi.org/
  46. Jonathan Parr. Carbon, silicon, germanium, tin and lead. Annual Reports Section "A" (Inorganic Chemistry) 2011, 107 , 83. https://doi.org/10.1039/c1ic90018h
  47. Hui-Xian Yeong, Hong-Wei Xi, Kok Hwa Lim, Cheuk-Wai So. Synthesis and Characterization of an Amidinate-Stabilized cis-1,2-Disilylenylethene [cis-LSi{C(Ph)C(H)}SiL] and a Singlet Delocalized Biradicaloid [LSi(μ2-C2Ph2)2SiL]. Chemistry - A European Journal 2010, 16 (43) , 12956-12961. https://doi.org/10.1002/chem.201001141
  48. David Gau, Tsuyoshi Kato, Nathalie Saffon-Merceron, Abel De Cózar, Fernando P. Cossío, Antoine Baceiredo. Synthesis and Structure of a Base-Stabilized C-Phosphino-Si-Amino Silyne. Angewandte Chemie 2010, 122 (37) , 6735-6738. https://doi.org/10.1002/ange.201003616
  49. David Gau, Tsuyoshi Kato, Nathalie Saffon-Merceron, Abel De Cózar, Fernando P. Cossío, Antoine Baceiredo. Synthesis and Structure of a Base-Stabilized C-Phosphino-Si-Amino Silyne. Angewandte Chemie International Edition 2010, 49 (37) , 6585-6588. https://doi.org/10.1002/anie.201003616
  50. Joon Soo Han, Takahiro Sasamori, Yoshiyuki Mizuhata, Norihiro Tokitoh. ChemInform Abstract: Reactivity of an Aryl-Substituted Silicon-Silicon Triple Bond: Reactions of a 1,2-Diaryldisilyne with Alkenes.. ChemInform 2010, 41 (29) , no-no. https://doi.org/10.1002/chin.201029187
  51. Owen T. Summerscales, Xinping Wang, Philip P. Power. Cleavage of the SnSn Multiple Bond in a Distannyne by Cyclooctatetraene: Formation of the π-Bound Inverse Sandwich Complex [(Ar′Sn)2(μ2-η2:η3-cot)]. Angewandte Chemie 2010, 122 (28) , 4898-4900. https://doi.org/10.1002/ange.201001276
  52. Owen T. Summerscales, Xinping Wang, Philip P. Power. Cleavage of the SnSn Multiple Bond in a Distannyne by Cyclooctatetraene: Formation of the π-Bound Inverse Sandwich Complex [(Ar′Sn)2(μ2-η2:η3-cot)]. Angewandte Chemie International Edition 2010, 49 (28) , 4788-4790. https://doi.org/10.1002/anie.201001276
  53. Joon Soo Han, Takahiro Sasamori, Yoshiyuki Mizuhata, Norihiro Tokitoh. Reactivity of an aryl-substituted silicon–silicon triple bond: 1,2-disilabenzenes from the reactions of a 1,2-diaryldisilyne with alkynes. Dalton Transactions 2010, 39 (39) , 9238. https://doi.org/10.1039/c0dt00115e

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