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[3.3.2]- and [3.3.3]Propellanes in Reactions with Oxidizing Electrophiles

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Abstract

The structure of [3.3.2]- and [3.3.3]propellanes, their framework analogs, and their radical-cations was investigated by computational methods (BLYP and B3LYP) in the 6-31G* basis set. The reactivity of the propellanes toward model oxidizing electrophiles does not contradict the quantum-chemical calculations. In the case of the tetracyclic framework analog of [3.3.3]propellane the reaction takes place as C—H substitution, whereas in the case of [3.3.2]propellanes it takes place as C—C-oxidative addition.

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Authors and Affiliations

  1. National Technical University of Ukraine "Kyiv Polytechnic Institute,", 37 Peremogy Prospekt, 03056, Kyiv, Ukraine

    T. E. Shubina, P. A. Gunchenko, T. S. Vigovskaya, A. G. Yurchenko & A. A. Fokin

  2. Department of Chemistry, University of Georgia, Athens, Georgia, 30602, USA

    P. R. Schreiner

Authors
  1. T. E. Shubina
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  2. P. A. Gunchenko
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  3. T. S. Vigovskaya
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  4. P. R. Schreiner
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  5. A. G. Yurchenko
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  6. A. A. Fokin
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Shubina, T.E., Gunchenko, P.A., Vigovskaya, T.S. et al. [3.3.2]- and [3.3.3]Propellanes in Reactions with Oxidizing Electrophiles. Theoretical and Experimental Chemistry 38, 229–236 (2002). https://doi.org/10.1023/A:1020511730749

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  • DOI: https://doi.org/10.1023/A:1020511730749

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