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Cyclic unsaturated compounds

Communication 39. Migration of methyl groups in 1-14CH3,2,3,4-tetramethylcyclopentadiene

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Conclusions

  1. 1.

    1-14CH3,2,3,4-Tetramethylcyclopentadiene was synthesized and its thermal transformations were studied.

  2. 2.

    An intramolecular 1,2-shift of the methyl group is realized in the tetramethylcyclopentadiene at temperatures exceeding 400°, which leads to an equilibrium distribution of the label between the C(1)-14CH3 (or C(4)-14CH3) and the C(2)-14CH3 (or C(3)-14CH3) positions when equilibrium is reached.

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Literature cited

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    V. A. Mironov, A. P. Ivanov, Ya. M. Kimelfeld, L. I. Petrovskaya, and A. A. Akhrem, Tetrahedron Lett., 3347 (1969).

  2. 2.

    V. A. Mironov, A. P. Ivanov, and A. A. Akhrem, Izv. Akad, Nauk SSSR, Ser. Khim., 1896 (1968).

  3. 3.

    V. A. Mironov, A. P. Ivanov, Ya. M. Kimel'fel'd, and A. A. Akhrem, Izv. Akad. Nauk SSSR, Ser. Khim., 1963 (1971).

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    V. A. Mironov, A. P. Ivanov, Ya. M. Kimel'fel'd, and A. A. Akhrem, Izv. Akad. Nauk SSSR, Ser. Khim., 1978 (1971).

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    V. A. Mironov, E. V. Sobolev, and A. N. Elizarova, Dokl. Akad. Nauk SSSR,143, 1112 (1962).

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    V. A. Mironov, T. M. Fadeeva, E. V. Sobolev, and A. N. Elizarova, Zh. Obshch. Khim.,33, 84 (1963).

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    V. A. Mironov, E. V. Sobolev, and A. N. Elizarova, Tetrahedron,19, 1939 (1963).

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    V. A. Mironov, T. M. Fadeeva, V. S. Pashegorova, Ya. M. Kimel'fel'd, and A. A. Akhrem, Izv.Akad. Nauk SSSR, Ser. Khim., 609 (1968).

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    V. A. Mironov, V. S. Pashegorova, T. M. Fadeeva, and A. A. Akhrem, Izv. Akad. Nauk SSSR, Ser. Khim., 182 (1968).

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    V. A. Mironov, V. S. Pashegorova, T. M. Fadeeva, and A. A. Akhrem, Tetrahedron Lett., 3997 (1968).

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    K. Alder and S. Schneider, Ann. Chem.,524, 189 (1936).

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Additional information

See [1] for Communication 38.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2253–2260, October, 1971.

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Mironov, V.A., Ivanov, A.P., Isagulyants, G.V. et al. Cyclic unsaturated compounds. Russ Chem Bull 20, 2128–2134 (1971). https://doi.org/10.1007/BF00851264

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Keywords

  • Methyl
  • Equilibrium Distribution
  • Unsaturated Compound
  • Thermal Transformation
  • Cyclic Unsaturated Compound