Mechanism of the Fischer reaction. Rearrangement of cyclohexanone N-methylphenylhydrazone and N,N′-dimethyl-N-phenyl-N′-(1-cyclohexenyl)hydrazine to 9-methyl-1,2,3,4-tetrahydrocarbazole |
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| Authors: | Przheval'skii N M Kletskii M E Grandberg I I Kostromina L Yu |
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| Institution: | (1) K. A. Timiryazev Moscow Agricultural Academy, 127550 Moscow;(2) Scientific-Research Institute for Physical and Organic Chemistry, M. A. Suslov Rostov State University, 344090 Rostovon-Don |
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| Abstract: | The kinetics of the thermal and acid-catalyzed Fischer reaction of cyclohexanone N-methylphenylhydrazone and N,N -dimethyl-N-pheny1-N-(1-cyclohexenyl)hydrazine were studied by a spectrophotometric method. Formation of the carbon-carbon bond proceeds by a 3,3]-sigmatropic shift mechanism. This conclusion was confirmed by MINDO/3 calculations of the rearrangement of a model divinylhydrazine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 779–787, June, 1985. |
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