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Effects of the medium on kinetics of transannular addition of iodine to dienes of the bicyclo[3.3.1]nonane series

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Abstract

The kinetics of the transannular iodination of 3, 7-dimethylene- and 3-methylene-7-isopropylidenebicyclo[3.3.1]nonane in benzene, toluene, dioxane, diethyl ether, and tetrahydrofuran have been investigated. The reactions obey a kinetic equation of the form w = k3[diene][I2]2. The reaction rate is determined by both the electrostatic and electron-donor parameters of the medium. A dependence of the effect of specific solvation with a maximum has been observed due to the different directions of the effects of electron donors of different strength. The results obtained have been described in the framework of a scheme of a molecular-ionic mechanism.

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Translated from Teoreticheskaya i Éksperimental'naya Khimiya, Vol. 25, No. 2, pp. 249–253, March–April, 1989.

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Khotkevich, A.B., Serguchev, Y.A., Krasutskii, P.A. et al. Effects of the medium on kinetics of transannular addition of iodine to dienes of the bicyclo[3.3.1]nonane series. Theor Exp Chem 25, 227–231 (1989). https://doi.org/10.1007/BF01135019

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Keywords

  • Ether
  • Benzene
  • Toluene
  • Iodine
  • Diethyl