Investigation of substituted bicyclo[4.2.0]oct-7-en-2-ones by13C NMR spectroscopy

  • M. I. Struchkova
  • A. Kh. Margaryan
  • É. P. Serebryakov
Physical Chemistry
Received:
  • 17 Downloads

Conclusions

  1. 1.

    The isomeric structures in the series of bicyclo[4.2.0]oct-7-en-2-one series were identified by the13C NMR method on the basis of the effect of the substituents.

     
  2. 2.

    The variations in the chemical shifts of the olefinic13C and1H in the 7-or 8-alkyl-substituted bicyclo[4.2.0]oct-7-en-2-ones under the influence of Eu(dpm)3 confirm the structural assignments in the investigated series of compounds.

     
  3. 3.

    The formation of the complex between 8-butylbieyclo[4.2.0]oct-7-en-2-one and Eu(dpm)3 leads to conformational changes.

     

Keywords

Spectroscopy Chemical Shift Conformational Change Isomeric Structure Structural Assignment 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
This is a preview of subscription content, log in to check access.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    A. Kh. Margaryan, É. P. Serebryakov, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim.,408 (1978).Google Scholar
  2. 2.
    S. D. Kulomzina, É. P. Serebryakov, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 2055 (1974).Google Scholar
  3. 3.
    É. P. Serebryakov, S. D. Kulomzina, A. Kh. Margaryan, and O. S. Chizhov, Izv. Akad. Nauk SSSR, Ser. Khim., 1728 (1977).Google Scholar
  4. 4.
    T. Pekh and E. Lippmaa, Org. Magn. Reson.,3, 679 (1971).Google Scholar
  5. 5.
    F. J. Weigert and J. D. Roberts, J. Am. Chem. Soc.,92, 1347 (1970); J. D. Roberts, F. J. Weigert, J. I. Kroschwitz, and J. H. Reich, J. Am. Chem. Soc.,92, 1338 (1970).Google Scholar
  6. 6.
    J. B. Grutzner, M. Lautelat, J. B. Dence, J. A. Smith, and J. D. Roberts, J. Am. Chem. Soc.,92, 7107 (1970).Google Scholar
  7. 7.
    G. S. Poindexter and P. J. Cropp, J. Org. Chem.,41, 1215 (1976).Google Scholar
  8. 8.
    G. Kean, D. Gravel, and S. Flizar, J. Am. Chem. Soc.,98, 4749 (1976).Google Scholar
  9. 9.
    R. A. Friedel and H. L. Retcofsky, J. Am. Chem. Soc.,85, 1300 (1963).Google Scholar
  10. 10.
    D. E. Dorman, M. Lautelat, and J. D. Roberts, J. Org. Chem.,36, 2757 (1971).Google Scholar
  11. 11.
    H. Hüther and H. A. Brune, Org. Magn. Reson.,3, 737 (1971).Google Scholar
  12. 12.
    G. C. Levy and D. C. Ditmer, Org. Magn. Reson.,4, 197 (1972).Google Scholar
  13. 13.
    J. Briggs, F. A. Hart, G. P. Moss, and E. W. Randall, Chem. Commun., 364 (1971).Google Scholar
  14. 14.
    R. Cargill and J. W. Crawford, J. Org. Chem.,35, 356 (1970).Google Scholar
  15. 15.
    O. A. Gansow and W. Schittenhelm, J. Am. Chem. Soc.,93, 4294 (1971).Google Scholar

Copyright information

© Plenum Publishing Corporation 1980

Authors and Affiliations

  • M. I. Struchkova
    • 1
  • A. Kh. Margaryan
    • 1
  • É. P. Serebryakov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

Personalised recommendations