Chemistry of Heterocyclic Compounds p. 713 - 722 (1986)
Update date:2022-08-03
Topics:
Visotskii, Yu. B.
Przheval'skii, N. M.
Zemskii, B. P.
Grandberg, I. I.
Kostromina, L. Yu.
Calculations of a number of model structures within the scheme of Fischer indole synthesis were made on the basis of a bonding variant of perturbation theory in the self-consistent-field (SCF) MO LCAO method.A quantum-chemical interpretation of the effect of substituents on the course of the thermal process is given.The kinetics of the thermal and acid-catalyzed indolization of substituted cyclohexanone arylhydrazones to tetrahydrocarbazoles were studied by spectrophotometry.It was shown that the experimental data are in satisfactory agreement with the calculated values. It was concluded that a concerted mechanism ( a <3,3>-sigma-tropic shift) for the step involving the formation of a carbon-carbon bond in the Fischer reaction is preferred.
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