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Cyclic unsaturated compounds

Communication 46. Synthesis and thermal isomerization of the 5,5-dimethyl-, 1,5,5-trimethyl-, and 1,4,5,5-tetramethylcyclopentadienes

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    5,5-Dimethylcyclopentadiene undergoes irreversible thermal isomerization at 220–330° to an equilibrium mixture of the 1,2-dimethyl-substituted cyclopentadienes, which proceeds by the mechanism of an intramolecular 1,2-shift of the alkyl group from the 5 position of the cyclopentadiene ring.

  2. 2.

    1,4,5,5-Tetramethylcyclopentadiene is isomerized at 250–380° to an equilibrium mixture of the 1,2,3,4-tetramethylcyclopentadienes as the result of two successive acts of an intramolecular 1,2-shift of the methyl group.

  3. 3.

    During the thermal transformations of the 5,5-disubstituted cyclopentadienes, containing substituents in the 1 and 4 positions, a reversible intramolecular 1,2-migration of the alkyl group is realized, without dis disturbing the geminal substitution.

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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. P. Ivanov & A. A. Akhrem

Authors
  1. V. A. Mironov
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  2. A. P. Ivanov
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  3. A. A. Akhrem
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No.2, pp. 363–370, February, 1973.

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Mironov, V.A., Ivanov, A.P. & Akhrem, A.A. Cyclic unsaturated compounds. Russ Chem Bull 22, 346–352 (1973). https://doi.org/10.1007/BF00850989

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  • DOI: https://doi.org/10.1007/BF00850989

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