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Stable Strained Donor-Free Silanone and Its Derived NHC-Stabilized Disilacyclobutadiene and Cyclic Alkenyl Silylene
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    Stable Strained Donor-Free Silanone and Its Derived NHC-Stabilized Disilacyclobutadiene and Cyclic Alkenyl Silylene
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    • Yazhou Ding
      Yazhou Ding
      State Key Laboratory of Elemento-Organic Chemistry and Frontiers Science Center of New Organic Matter, Nankai University, Tianjin 300071, People’s Republic of China
      More by Yazhou Ding
    • Wen Jin
      Wen Jin
      State Key Laboratory of Elemento-Organic Chemistry and Frontiers Science Center of New Organic Matter, Nankai University, Tianjin 300071, People’s Republic of China
      More by Wen Jin
    • Chen-Huan Liu
      Chen-Huan Liu
      State Key Laboratory of Elemento-Organic Chemistry and Frontiers Science Center of New Organic Matter, Nankai University, Tianjin 300071, People’s Republic of China
    • Jianying Zhang
      Jianying Zhang
      State Key Laboratory of Elemento-Organic Chemistry and Frontiers Science Center of New Organic Matter, Nankai University, Tianjin 300071, People’s Republic of China
    • Chunming Cui*
      Chunming Cui
      State Key Laboratory of Elemento-Organic Chemistry and Frontiers Science Center of New Organic Matter, Nankai University, Tianjin 300071, People’s Republic of China
      *Email: [email protected]
      More by Chunming Cui
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2024, 146, 40, 27312–27317
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    https://doi.org/10.1021/jacs.4c11194
    Published September 26, 2024
    Copyright © 2024 American Chemical Society

    Abstract

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    The strained silanone 2 was obtained by the reaction of disilacyclobutene 1 with N2O. Silanone 2 exhibited unprecedented thermal stability in both the solid state and solution. DFT calculations on 2 revealed that the highly polarized Si═O double bond is effectively stabilized by its electron delocalization with the unsaturated Si2C2 ring. Treatment of 2 with 1,3,4,5-tetramethylimidazolin-2-ylidene yielded the first Lewis base-stabilized disilacyclobutadiene 3 via a 1,3-boryl migration. Reaction of 2 with HCCH and Me3SiN3 resulted in the addition of C–H and Si–N bonds to the Si═O double bond. Interestingly, irradiation of 2 at rt yielded oxosilanes 7A and 7B in C6D6 and n-hexane, respectively, via the 1,2-boryl migration and ring expansion, whereas photolysis at −60 °C led to the formation of cyclic alkenyl silylene 8.

    Copyright © 2024 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.4c11194.

    • Experimental part, including synthesis and spectroscopic characterization of new compounds, X-ray crystal diffraction analysis, and results of DFT calculations (PDF)

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    CCDC 2367921, 23767762376778, 23767802376782, and 2376784 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    This article is cited by 1 publications.

    1. Falk Ebeler, Beate Neumann, Hans-Georg Stammler, Israel Fernández, Rajendra S. Ghadwal. Structural Snapshots of Reversible Carbon Dioxide Capture and (De)oxygenation at Group 14 Diradicaloids. Journal of the American Chemical Society 2024, 146 (50) , 34979-34989. https://doi.org/10.1021/jacs.4c15062

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2024, 146, 40, 27312–27317
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.4c11194
    Published September 26, 2024
    Copyright © 2024 American Chemical Society

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