Skip to main content
SpringerLink
Log in

Quantum-chemical interpretation of recyclization reactions. 7. Isoelectronic analogs of the benzyl cation. Heterofulvenes

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The effect of the nature of the heteroatom, annelation, the position of the methylene group, and the character of the substituent on expansion of the ring of heterofulvene cations was investigated on the basis of the bonded variant of perturbation theory within the framework of the π-electron approach. The rearrangements of 1-methylene-3-oxoisofuran, 2-methylene-3-oxobenzofuran, and N-methyleneisoxazole ylid were also examined. The results of the calculations are in agreement with the experimental data.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. Yu. B. Vysotskii and B. P. Zemskii, Khim. Geterotsikl. Soedin., No. 12, 1673 (1982).

    Google Scholar 

  2. Yu. B. Vysotskii, N. A. Kovach, and O. P. Shvaika, Khim. Geterotsikl. Soedin., No. 9, 1186 (1977).

    Google Scholar 

  3. Yu. B. Vysotskii and L. N. Sivyakova, Zh. Struk. Khim., 21, 164 (1980).

    Google Scholar 

  4. Yu. B. Vysotskii, B. P. Zemskii, E. A. Zemskaya, and N. N. Alekseev, Zh. Struk. Khim., 22, No. 3, 13 (1981).

    Google Scholar 

  5. P. B. Terent'ev, Mass Spectrometry in Organic Chemistry [in Russian], Vysshaya Shkola, Moscow (1979), p. 222.

    Google Scholar 

  6. Q. N. Porter and I. Balda, Mass Spectrometry of Heterocyclic Compounds, Interscience, New York-London-Sydney-Toronto (1971), p. 564.

    Google Scholar 

  7. G. Speteller, in: Physical Methods in Heterocyclic Chemistry, Vol. 3, edited by A. R. Katritzky, Academic Press, New York-London (1971), p. 223.

    Google Scholar 

  8. G. Spliter, Adv. Heterocycl. Chem., 7, 301 (1966).

    Google Scholar 

  9. R. A. Iones, Adv. Heterocycl. Chem., 11, 383 (1970).

    Google Scholar 

  10. Catalog of Concise Mass Spectra [in Russian], Nauka, Novosibirsk (1981), p. 185.

  11. V. I. Ivanskii, The Chemistry of Heterocyclic Compounds [in Russian], Vysshaya Shkola, Moscow (1978), p. 559.

    Google Scholar 

  12. N. Pukhotin, Zh. Russk. Fiz.-khim. Ova., 59, 761 (1927).

    Google Scholar 

  13. A. Pictet, Chem. Ber., 38, 1946 (1905).

    Google Scholar 

  14. N. I. Putokhin, Zh. Russk. Fiz.-khim. Ova., 62, 2226 (1930).

    Google Scholar 

  15. N. I. Putokhin and V. S. Egorova, Dokl. Akad. Nauk SSSR, 96, 293 (1954).

    Google Scholar 

  16. Yu. B. Vysotskii, B. P. Zemskii, T. V. Stupnikova, and R. S. Sagitullin, Khim. Geterotsikl. Soedin., No. 6, 779 (1981).

    Google Scholar 

  17. B. Iddon and R. M. Scrowston, Adv. Heterocycl. Chem., 11, 177 (1970).

    Google Scholar 

  18. H. C. Van der Plas, Ring Transformations of Heterocycles, Vol. 1, Academic Press, London-New York (1973), p. 484.

    Google Scholar 

  19. Yu. B. Vysotskii, N. A. Kovach, and O. P. Shvaika, Izv. Sibirsk. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, No. 2, 3 (1980).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Physical Organic Chemistry and Coal Chemistry, Academy of Sciences of the Ukrainian SSR, 340048, Donetsk

    Yu. B. Vysotskii & B. P. Zemskii

  2. Donetsk State University, 340055, Donetsk

    Yu. B. Vysotskii & B. P. Zemskii

Authors
  1. Yu. B. Vysotskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. B. P. Zemskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 341–349, March, 1983.

See[1] for communication 6.

The authors thank O. P. Shvaika, who directed their attention to the research of N. I. Putchin.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Vysotskii, Y.B., Zemskii, B.P. Quantum-chemical interpretation of recyclization reactions. 7. Isoelectronic analogs of the benzyl cation. Heterofulvenes. Chem Heterocycl Compd 19, 276–282 (1983). https://doi.org/10.1007/BF00513259

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00513259

Keywords

Search

Navigation