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Mechanism of Fischer reaction. Dependence of thermal indolization of cyclohexanone arylhydrazones on nature of substituent in the benzene ring

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The kinetics of the Fischer thermal indolization of monosubstituted cyclohexanone arylhydrazones was studied by the spectrophotometric method. The enthalpy and entropy of activation of the reaction were calculated. The data obtained were interpreted in terms of a consistent mechanism of formation of a carbon-carbon bond (the [3,3]-sigmatropic shift). It was found that the influence of the electronic factors on the rate of the sigmatropic rearrangement is inappreciable.

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Authors and Affiliations

  1. K. A. Timiryazev Moscow Agricultural Academy, 127550, Moscow

    N. M. Przheval'skii, L. Yu. Kostromina & I. I. Grandberg

Authors
  1. N. M. Przheval'skii
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  2. L. Yu. Kostromina
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  3. I. I. Grandberg
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 188–192, February, 1988.

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Przheval'skii, N.M., Kostromina, L.Y. & Grandberg, I.I. Mechanism of Fischer reaction. Dependence of thermal indolization of cyclohexanone arylhydrazones on nature of substituent in the benzene ring. Chem Heterocycl Compd 24, 154–158 (1988). https://doi.org/10.1007/BF00473323

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  • DOI: https://doi.org/10.1007/BF00473323

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