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Cyclic unsaturated compounds Communication 54. Synthesis and thermal transformations of methyl-1,3-cyclohexadienes

  • Organic and Biological Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    Migration of the system of double bonds in 1,3-cyclohexadienes is accomplished at temperatures exceeding 300° as the result of the reversible thermal intramolecular 1,5-shift of hydrogen. A thermodynamic equilibrium is established under the indicated conditions between the isomeric 5-(I), 1-(II), and 2-(III)-methyl-1,3-cyclohexadienes.

  2. 2.

    Besides the 1,2-elimination of the elements of water, 1,4-elimination occurs during the dehydration of allylic 2-cyclohexen-1-ols.

  3. 3.

    At 460–500° the methyl-1,3-cyclohexadienes undergo thermal dehydrogenation to toluene, accompanied by the formation of only insignificant amounts of methylcyclohexenes.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, USSR

    V. A. Mironov, A. D. Fedorovich & A. A. Akhrem

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  1. V. A. Mironov
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  2. A. D. Fedorovich
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  3. A. A. Akhrem
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2036–2045, September, 1973.

See [1] for Communication 53; see [2] for preliminary communication.

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Mironov, V.A., Fedorovich, A.D. & Akhrem, A.A. Cyclic unsaturated compounds Communication 54. Synthesis and thermal transformations of methyl-1,3-cyclohexadienes. Russ Chem Bull 22, 1984–1991 (1973). https://doi.org/10.1007/BF00929389

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  • DOI: https://doi.org/10.1007/BF00929389

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