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Syntheses and Structures of Stable 1-Aminoalumole Derivatives

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Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan
*Tel: +81-774-38-3200. Fax: +81-774-38-3209. E-mail: [email protected]. Web: http://boc.kuicr.kyoto-u.ac.jp/www/index-e.html.
Cite this: Organometallics 2014, 33, 23, 6963–6966
Publication Date (Web):November 19, 2014
https://doi.org/10.1021/om501055f
Copyright © 2014 American Chemical Society
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Abstract

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Reaction of an isolable 1-bromoalumole with LiN(SiMe3)2 in toluene afforded a lithium 1,1-diaminodialumoluide, while in THF the corresponding 1-aminoalumole–THF complex was obtained. These amino-substituted alumole derivatives are characterized by X-ray crystallographic analysis and NMR spectroscopy. The lithium 1,1-diaminoalumoluide and the 1-aminoalumole–THF complex were converted to each other by ligand exchange reactions.

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NMR spectra, a CIF file giving full crystallographic data for compounds 5 and 6, a text file of all computed molecule Cartesian coordinates in a format for convenient visualization, and complete citation for ref 22. 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 17 publications.

  1. Yongliang Zhang, Junnian Wei, Wen-Xiong Zhang, and Zhenfeng Xi . Lithium Aluminate Complexes and Alumoles from 1,4-Dilithio-1,3-Butadienes and AlEt2Cl. Inorganic Chemistry 2015, 54 (22) , 10695-10700. https://doi.org/10.1021/acs.inorgchem.5b01551
  2. Takuya Matsumoto, Hirofumi Takamine, Kazuo Tanaka, and Yoshiki Chujo . Synthesis of Air- and Moisture-Stable Dibenzogallepins: Control of Planarity of Seven-Membered Rings in Solid States by Coordination to Gallium Atoms. Organic Letters 2015, 17 (6) , 1593-1596. https://doi.org/10.1021/acs.orglett.5b00489
  3. Takuya Matsumoto, Kazuo Tanaka, and Yoshiki Chujo . Synthesis and Characterization of Gallafluorene-Containing Conjugated Polymers: Control of Emission Colors and Electronic Effects of Gallafluorene Units on π-Conjugation System. Macromolecules 2015, 48 (5) , 1343-1351. https://doi.org/10.1021/ma502592c
  4. Regina Drescher, Shujuan Lin, Alexander Hofmann, Carsten Lenczyk, Stephanie Kachel, Ivo Krummenacher, Zhenyang Lin, Holger Braunschweig. Ring expansion of alumoles with organic azides: selective formation of six-membered aluminum–nitrogen heterocycles. Chemical Science 2020, 11 (21) , 5559-5564. https://doi.org/10.1039/D0SC02032J
  5. Alexander Sadimenko. Boroles and analogs. 2020,,, 711-743. https://doi.org/10.1016/B978-0-08-102860-5.00006-7
  6. . Organometallic Chemistry of Five-Membered Heterocycles. 2020,,https://doi.org/
  7. A.P. Sadimenko. Five-membered Rings with Other Elements. 2020,,https://doi.org/10.1016/B978-0-12-409547-2.14790-0
  8. . Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. 2020,,https://doi.org/
  9. Xiao Chen, Michael T. Gamer, Peter W. Roesky. Synthesis and structural characterization of arsinoamides – early transition metal (Zr and Hf) and main group metal (Al, In, Sn, and Pb) complexes. Dalton Transactions 2019, 48 (40) , 15207-15211. https://doi.org/10.1039/C9DT03472B
  10. Yongliang Zhang, Zhenqiang Yang, Wen‐Xiong Zhang, Zhenfeng Xi. Indacyclopentadienes and Aromatic Indacyclopentadienyl Dianions: Synthesis and Characterization. Chemistry – A European Journal 2019, 25 (16) , 4218-4224. https://doi.org/10.1002/chem.201806356
  11. Tomohiro Agou, Norihiro Tokitoh. Reactivity of Organoaluminum Compounds with Unique Coordination Modes. Journal of Synthetic Organic Chemistry, Japan 2017, 75 (7) , 723-734. https://doi.org/10.5059/yukigoseikyokaishi.75.723
  12. Norihiro Tokitoh, Tomohiro Agou, Tatsuya Wasano, Takahiro Sasamori. Synthesis and properties of stable alumoles. Phosphorus, Sulfur, and Silicon and the Related Elements 2016, 191 (4) , 584-587. https://doi.org/10.1080/10426507.2015.1128911
  13. Takako Muraoka, Taro Nakashima, Mizuki Ogashiwa, Keiji Ueno. Synthesis and Structure of η 1 -Gallacyclopentadienyl Complexes. Chemistry Letters 2016, 45 (1) , 39-41. https://doi.org/10.1246/cl.150919
  14. Tomohiro Agou, Tatsuya Wasano, Takahiro Sasamori, Jing-Dong Guo, Shigeru Nagase, Norihiro Tokitoh. Ring Expansion to 1-Bromo-1-alumacyclonona-2,4,6,8-tetraene by Insertion of Two Alkyne Molecules into the AlC Bonds. Angewandte Chemie 2015, 127 (33) , 9704-9707. https://doi.org/10.1002/ange.201504468
  15. Tomohiro Agou, Tatsuya Wasano, Takahiro Sasamori, Jing-Dong Guo, Shigeru Nagase, Norihiro Tokitoh. Ring Expansion to 1-Bromo-1-alumacyclonona-2,4,6,8-tetraene by Insertion of Two Alkyne Molecules into the AlC Bonds. Angewandte Chemie International Edition 2015, 54 (33) , 9568-9571. https://doi.org/10.1002/anie.201504468
  16. Takuya Matsumoto, Kazuo Tanaka, Kazuyoshi Tanaka, Yoshiki Chujo. Synthesis and characterization of heterofluorenes containing four-coordinated group 13 elements: theoretical and experimental analyses and comparison of structures, optical properties and electronic states. Dalton Transactions 2015, 44 (18) , 8697-8707. https://doi.org/10.1039/C5DT00718F
  17. Takuya Matsumoto, Kazuo Tanaka, Yoshiki Chujo. High HOMO levels and narrow energy band gaps of dithienogalloles. RSC Advances 2015, 5 (68) , 55406-55410. https://doi.org/10.1039/C5RA08584E

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