Abstract
Mechanisms of reactions of brominated diolefins of the bicyclo[3.3.1]nonane series were studied. The reaction of transannular cyclization into adamantane derivatives proceeds by a molecular-ionic mechanism, and the rate of reaction obeys a third-order kinetic equation. An analysis of the calculated thermodynamic parameters of the transition state shows that intermediate complexes with charge transfer of the diolefin...Br2 and diolefin...Br4 type are formed.
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Translated from Teoreticheskaya i Éksperimental'naya Khimiya, Vol. 21, No. 1, pp. 52–56, January–February, 1985.
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Krasutskii, P.A., Khotkevich, A.B., Serguchev, Y.A. et al. Mechanism of transannular bromination reactions of diolefins of the bicyclo[3.3.1]nonane series. Theor Exp Chem 21, 48–52 (1985). https://doi.org/10.1007/BF00524310
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DOI: https://doi.org/10.1007/BF00524310