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Quantum-Chemical Study of the Mechanism and Regioselectivity of Transannular Cyclization of Dienes of the Bicyclo[3.3.1]nonane Series Treated with Bromosuccinimide and F-TEDA-BF4

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Abstract

We have shown that, in transannular cyclization of 3,7-bismethylenebicyclo[3.3.1]nonane derivatives with methyl or phenyl substituents in one of the exocyclic methylene groups, when N-bromosuccinimide is used the bromine atom is added to the unsubstituted double bond; and when the electrophilic fluorinating reagent F-TEDA-BF4 is used, the bromine atom is added to the substituted double bond. We have used the PM3 semiempirical method to study the mechanism of these reactions.

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmans'ka Vul., 02094, Kyiv, Ukraine

    A. M. Nesterenko, M. V. Ponomarenko, L. F Lur'e & Yu. A. Serguchev

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  1. A. M. Nesterenko
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  2. M. V. Ponomarenko
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  3. L. F Lur'e
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  4. Yu. A. Serguchev
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Nesterenko, A.M., Ponomarenko, M.V., Lur'e, L.F. et al. Quantum-Chemical Study of the Mechanism and Regioselectivity of Transannular Cyclization of Dienes of the Bicyclo[3.3.1]nonane Series Treated with Bromosuccinimide and F-TEDA-BF4 . Theoretical and Experimental Chemistry 38, 156–161 (2002). https://doi.org/10.1023/A:1019648817601

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