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Cyclic unsaturated compounds. 65. Cycloheptadienyl anions

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

Conclusions

  1. 1.

    The thermal isomerization of 1,3- and 1,4-cycloheptadiene is not observed up to 500°C.

  2. 2.

    In the presence of a strong base, 1,4-cycloheptadienes isomerize almost irreversibly to the corresponding 1,3-dienes; bases do not catalyze double-bond migration in the 1,3-cycloheptadiene series.

  3. 3.

    For the reaction of 1,3- and 1,4-cycloheptadienes with a strong base the formation of anions that can be alkylated occurs; these anions are not identical and, therefore, do not have the structure of a homocyclopentadienyl anion.

  4. 4.

    A correlation between the acidity of the hydrocarbons in the series eyclopentadiene-cyclohexadiene-cycloheptadiene and the enthalpy of activation for double-bond migration in the same series does not exist. Consequently, in this isomerization process the migrating hydrogen atom does not have a positive charge.

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Authors and Affiliations

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

    V. A. Mironov, A. D. Federovich, O. M. Nefedov & A. A. Akhrem

  2. Moscow Technological Institute for the Meat and Dairy Industry, USSR

    V. A. Mironov, A. D. Federovich, O. M. Nefedov & A. A. Akhrem

Authors
  1. V. A. Mironov
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  2. A. D. Federovich
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  3. O. M. Nefedov
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  4. A. A. Akhrem
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 104–109, January, 1978.

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Mironov, V.A., Federovich, A.D., Nefedov, O.M. et al. Cyclic unsaturated compounds. 65. Cycloheptadienyl anions. Russ Chem Bull 27, 91–96 (1978). https://doi.org/10.1007/BF01153216

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  • DOI: https://doi.org/10.1007/BF01153216

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