Skip to main content
SpringerLink
Log in

2-Phenylsulfinylmethyl-1,3-butadiene in the thermal Diels-Alder reaction

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

Conclusions

  1. 1.

    The behavior of 2-phenylsulfinylmethylbuta-1,3-diene in the thermal Diels-alder reaction with symmetrical (N-phenylmaleimide, dimethylcyclopropene) and unsymmetrical (methyl vinyl ketone) dienophiles has been examined.

  2. 2.

    This reaction provides a simple method of preparing exomethylene allyl alcohols of the carane and p-menthane series which are difficult to obtain by other methods.

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. M. Petrzilka and J.' I. Grayson, Synthesis, 753 (1981); R. R. Schmidt, Acc. Chem. Res.,19, 250 (1986).

  2. T. Mandai, J. Yokoyama, T. Miki, et al., Chem. Lett., 1057 (1980).

  3. T. Mandai, K. Osaka, M. Kawagishi, et al., J. Org. Chem.,49, 3595 (1984).

    Google Scholar 

  4. P. J. Proteau and P. B. Hopkins, J. Org. Chem.,50, 141 (1985).

    Google Scholar 

  5. V. V. Veselovskii, Z. G. Makarova, A. I. Lutsenko, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 811 (1987).

  6. V. M. Zhulin and S. I. Volchek, Khim. Geterotsikl. Soedin., 1443 (1979).

  7. Z. G. Isaeva, G. A. Bakaleinik, and A. N. Karaseva, Izv. Akad. Nauk SSSR, Ser. Khim., 1651 (1983).

  8. A. N. Vereshchagin, Usp. Khim.,52, 1879 (1983).

    Google Scholar 

  9. A. M. Moiseenkov, B. A. Cheskis, A. B. Veselovskii, et al., Zh. Org. Khim.,23, 1852 (1987).

    Google Scholar 

  10. K. Gollnick and G. Schade, Tetrahedron,22, 133 (1966).

    Google Scholar 

  11. T. Kametani, H. Kurobe, and H. Nemoto, J. Chem. Soc. Perkin Trans, 1, 756 (1981).

    Google Scholar 

  12. Beilsteins Handbuch der Organischen Chemie, E. 2, Vol. 5, p. 95 (1943).

  13. W. J. Gensler and P. H. Solomon, J. Org. Chem.,38, 1726 (1973).

    Google Scholar 

  14. E. F. Lutz and G. M. Bailey, J. Am. Chem. Soc.,86, 3899 (1964).

    Google Scholar 

Download references

Author information

Authors and Affiliations

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

    V. V. Veselovskii, Z. G. Makarova, A. I. Lutsenko, N. A. Shpiro, V. M. Zhulin & A. M. Moiseenkov

Authors
  1. V. V. Veselovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Z. G. Makarova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. I. Lutsenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. A. Shpiro
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. M. Zhulin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. M. Moiseenkov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 810–815, April, 1988.

The authors thank V. V. Tyurin for assistance with some of the experiments.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Veselovskii, V.V., Makarova, Z.G., Lutsenko, A.I. et al. 2-Phenylsulfinylmethyl-1,3-butadiene in the thermal Diels-Alder reaction. Russ Chem Bull 37, 692–697 (1988). https://doi.org/10.1007/BF01455479

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01455479

Keywords

Search

Navigation