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Rearrangement of the halogen atom in halobarenes and haloneobarenes

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

Conclusions

  1. 1.

    The thermal rearrangement of the halogen in 9-halobarenes and 9-haloneobarenes yields all of the possible B-halobarenes and B-haloneobarenes.

  2. 2.

    The thermal rearrangement rate of the halogen in the 9-haloneobarenes is considerably slower than that of the halogen in the 9-halobarenes.

  3. 3.

    The rearrangement rate of the halogen in the haloneobarenes depends on the nature of the halogen.

  4. 4.

    The isomerization of the 9,12-dihalobarene, 8, 9,12-trihalobarene and 8, 9,10,12-tetrahalobarene proceeds with the formation of mixtures containing most of the corresponding isomeric haloneobarenes.

  5. 5.

    It was shown that the intermolecular exchange B-H+B-I⇌B-I+B-H takes place in the barenes.

  6. 6.

    The rate with which the hydrogen atom in the different positions of the neobarene nucleus is replaced during electrophilic halogenation decreases in the order: 9,10≫5,12>4,7,8,11≫2,3.

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Literature cited

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Authors and Affiliations

  1. Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, USSR

    L. I. Zakharkin & V. N. Kalinin

Authors
  1. L. I. Zakharkin
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  2. V. N. Kalinin
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 607–611, March, 1969.

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Zakharkin, L.I., Kalinin, V.N. Rearrangement of the halogen atom in halobarenes and haloneobarenes. Russ Chem Bull 18, 542–545 (1969). https://doi.org/10.1007/BF00906974

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  • DOI: https://doi.org/10.1007/BF00906974

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