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Determination of the Z, E configuration of functionally trisubstituted olefins by13C NMR

  • Physical Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The Z, E configuration of functional trisubstituted olefins was established by means of13C NMR.

  2. 2.

    CX, the constant of spin-spin coupling with the allyl protons of the R substituent, is characteristic; it is 5.0 and 3.5 Hz for E and Z isomers, respectively.

  3. 3.

    The chemical shift values for the olefinic carbon Cβ in α,β-unsaturated aldehydes permit the assumption that conjugation of the olefin bond is more effective in E isomers than in Z isomers.

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Literature cited

  1. N. Ya. Grigor'eva, E. P. Prokof'ev, and A. V. Semenovskii, Dokl Akad. Nauk SSSR,245, 366 (1979).

    Google Scholar 

  2. N. Ya Grigor'eva and A. V. Semenovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 2644 (1976).

  3. U. Vogeli and W. Philisborn, Org. Magn. Reson.,7, 617 (1975).

    Google Scholar 

  4. E. P. Prokof'eva and Zh. A. Krasnaya, Izv. Akad. Nauk SSSR, Ser. Khim., 2301 (1978).

  5. E. P. Prokof'eva, E. I. Karpeiskaya, G. B. Chel'tsova, and T. B. Dantsig, Izv. Akad. Nauk SSSR, Ser. Khim., 823 (1980).

  6. D. M. Grant and B. V. Cheney, J. Am. Chem. Soc.,89, 5315 (1967).

    Google Scholar 

  7. B. V. Cheney and D. M. Grant, J. Am. Chem. Soc.,89, 5319 (1967).

    Google Scholar 

  8. D. M. Marr and J. B. Stothers, Can. J. Chem.,43, 596 (1965).

    Google Scholar 

  9. O. A. Gansow and W. Schittenhelm, J. Am. Chem. Soc.,93, 4294 (1971).

    Google Scholar 

  10. G. C. Levy and G. L. Nelson, Carbon-13 Nuclear Magnetic Resonance for Organic Chemists, Wiley-Interscience (1972).

  11. J. B., Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York-London (1972), p. 80.

    Google Scholar 

  12. E. J. Corey and H. Yamamoto, J. Am. Chem. Soc.,92, 226 (1970).

    Google Scholar 

  13. E. J. Corey, N. W. Gilman, and B. E. Ganem, J. Am. Chem. Soc.,90, 5616 (1968).

    Google Scholar 

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 834–837, April, 1980.

Deceased.

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Prokof'ev, E.P., Grigor'eva, N.Y. & Semenovskii, A.V. Determination of the Z, E configuration of functionally trisubstituted olefins by13C NMR. Russ Chem Bull 29, 586–589 (1980). https://doi.org/10.1007/BF00961608

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  • DOI: https://doi.org/10.1007/BF00961608

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