Skip to main content
Log in

An unusual rearrangement and addition of solvent during the photolysis of alkyl-substituted bicyclo[3.2.0 ]hept-6-en-2-ones in methanol

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

Conclusions

During irradiation in methanol by light with λ ≥ 300 nm, 7-amyl- and 6-amylbicyclo[3.2.0]hept-6-en-2-ones rearrange into derivatives of bicyclo[2.2.1]heptene with the simultaneous addition of the solvent.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. N. N. Houk, Chem. Rev.,76, 1 (1976).

    Google Scholar 

  2. W. G. Dauben, G. Lodder, and J. Ipaktschi, Fortschr. Chem. Forsch.,54, 73 (1975).

    Google Scholar 

  3. P. L. Cargill, T. E. Jackson, N. P. Peet, and D. M. Pond, Accounts Chem. Res.,7, 106 (1974).

    Google Scholar 

  4. P. L. Cargill, D. M. Pond, and S. O. LeGrand, J. Org. Chem.,35, 359 (1970).

    Google Scholar 

  5. E. P. Serebryakov, S. D. Kulomzina, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 2739 (1975).

  6. E. J. Snyder and B. Franzus, J. Am. Chem. Soc.,86, 1166 (1964).

    Google Scholar 

  7. K. Tori, A. Aono, Y. Hata, R. Muneyuki, T. Tsuji, and H. Tanida, Tetrahedron Lett., 9 (1966).

  8. L. A. Paquette and G. Zon, J. Am. Chem. Soc.,94, 5096 (1972).

    Google Scholar 

  9. B. Franzus, W. C. Baird, N. F. Chamberlain, T. Hines, and E. J. Snyder, J. Am. Chem. Soc.,90, 3721 (1968).

    Google Scholar 

  10. A. P. Marchand and J. E. Rose, J. Am. Chem. Soc.,90, 3724 (1968).

    Google Scholar 

  11. J. B. Grutzner, M. Jautelat, J. B. Dence, R. A. Smith, and J. D. Roberts, J. Am. Chem. Soc.,92, 7107 (1970).

    Google Scholar 

  12. P. Yates, Pure and Appl. Chem.,16, 93 (1968).

    Google Scholar 

  13. P. H. Boyle, W. Cocker, D. H. Grayson, and P. V. P. Shannon, J. Chem. Soc. 1073 (C 1971).

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2760–2764, December, 1977.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Serebryakov, É.P., Kulomzina, S.D. & Kucherov, V.F. An unusual rearrangement and addition of solvent during the photolysis of alkyl-substituted bicyclo[3.2.0 ]hept-6-en-2-ones in methanol. Russ Chem Bull 26, 2551–2555 (1977). https://doi.org/10.1007/BF00924563

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00924563

Keywords

Navigation