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Unique stereochemistry of 3-borabicyclo[3.3.1]nonane derivatives

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Abstract

The conformational equilibrium in solution was examined by NMR spectroscopy for a series of 7α-phenyl-3-borabicyclo[3.3.1]nonane derivatives containing various substituents at the boron atom. The structures of these derivatives were studied in the crystalline state (X-ray diffraction analysis) and by quantum-chemical calculations (B3Pw91/6-31G*). The B...Ph transannular interactions corresponding to charge transfer from the π system of the phenyl group to the vacant p-orbital of the B atom were demonstrated to be responsible for unique stability of the chair-chair conformation of these derivatives.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    M. E. Gurskii, A. L. Karionova, P. A. Belyakov, T. V. Potapova & Yu. N. Bubnov

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    K. A. Lyssenko, M. Yu. Antipin & Yu. N. Bubnov

Authors
  1. M. E. Gurskii
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  2. K. A. Lyssenko
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  3. A. L. Karionova
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  4. P. A. Belyakov
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  5. T. V. Potapova
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  6. M. Yu. Antipin
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  7. Yu. N. Bubnov
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1884–1896, September, 2004.

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Gurskii, M.E., Lyssenko, K.A., Karionova, A.L. et al. Unique stereochemistry of 3-borabicyclo[3.3.1]nonane derivatives. Russ Chem Bull 53, 1963–1977 (2004). https://doi.org/10.1007/s11172-005-0057-2

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  • DOI: https://doi.org/10.1007/s11172-005-0057-2

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