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Thermal isomerization of 1,4,5,5-tetramethylcyclopentadiene

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Conclusions

  1. 1.

    At 310–460°, 1,4,5,5-tetramethylcylopentadiene (I) is thermally isomerized to a mixture of 1,2,3,4-(II), 1,2,3,5- (III), and 1,2,4,5-tetramethylcyclopentadienes (IV) without the formation of side products.

  2. 2.

    A combination of two successive intramolecular 1,2-shifts of a methyl group, accompanied in the final step by the establishment of thermodynamic equilibrium among isomers (II), (III), and (IV) as a result of a 1,2-hydrogen shift, is considered to be the mechanism of the isomerization.

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Literature cited

  1. 1.

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

  2. 2.

    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, Tetrahedron Lett., 3997 (1968).

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    V.A.Mironov, A.P.Ivanov, G.V.Isagulyants, L.I.Kovalenko, and A.A.Akhrem, Izv.Akad.Nauk SSSR, Ser.Khim., 2253 (1971).

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    V.A.Mironov, E.V.Sobolev, and A.N.Elizarova, Izv.Akad.Nauk SSSR, Ser.Khim., 1607 (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, A.P.Ivanov, Ya.M.Kimel'fel'd, and A.A.Akhrem, Izv.Akad.Nauk SSSR, Ser.Khim., 1977 (1971).

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1849–1851, August, 1972.

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Mironov, V.A., Ivanov, A.P. & Akhrem, A.A. Thermal isomerization of 1,4,5,5-tetramethylcyclopentadiene. Russ Chem Bull 21, 1788–1790 (1972). https://doi.org/10.1007/BF00851202

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Keywords

  • Methyl
  • Thermodynamic Equilibrium
  • Side Product
  • Thermal Isomerization