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Mechanism of the fischer reaction. Effect of electronic factors on the kinetics of the rearrangement of m-substituted cyclohexanone arylhydrazones to tetrahydrocarbazoles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The kinetics of the thermal and acid-catalyzed Fischer indolization of m-substituted cyclohexanone arylhydrazones were studied. It was shown that substituents with different natures (-CH3, -Cl) and the polarity of the solvent have little effect on the rate of the rearrangement. The results obtained were interpreted within the framework of a concerted mechanism for the formation of the carbon-carbon bond ([3,3]-sigmatropic rearrangement).

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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. 9, pp. 1207–1212, September, 1985.

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Przheval'skii, N.M., Kostromina, L.Y. & Grandberg, I.I. Mechanism of the fischer reaction. Effect of electronic factors on the kinetics of the rearrangement of m-substituted cyclohexanone arylhydrazones to tetrahydrocarbazoles. Chem Heterocycl Compd 21, 1002–1008 (1985). https://doi.org/10.1007/BF00515023

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  • DOI: https://doi.org/10.1007/BF00515023

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