13C NMR Spectra of substituted cyclopropanes

Communication 1. Chemical shifts of13C and absence of σπ-pπ interaction in cyclopropylalkyl ethers
  • G. A. Kalabin
  • D. F. Kushnarev
  • S. M. Shostakovskii
  • T. K. Voropaeva
Physical Chemistry
  • 35 Downloads

Conclusions

  1. 1.

    The13C NMR spectra of a number of eyclopropyl ethers were studied for the first time.

     
  2. 2.

    An analysis of the values of the chemical shifts of13C in cyclopropyl alkyl ethers indicates the absence of σπ-pπ conjugation between the ring and the oxygen atom in the ground state.

     

Keywords

Oxygen Ether Oxygen Atom Cyclopropane Cyclopropyl 
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.

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Literature cited

  1. 1.
    P. R. Schleyer and V. Buss, J. Amer. Chem. Soc.,91, 5880 (1969).Google Scholar
  2. 2.
    C. F. Wilcox, L. M. Loew, and R. Hoffmann, J. Amer. Chem. Soc.,95, 8192 (1973).Google Scholar
  3. 3.
    M. Yu. Lukina, Uspekhi Khimii,31, 901 (1962).Google Scholar
  4. 4.
    M. Charton, Progress in Physical Organic Chemistry, Vol. 10, Wiley, New York (1973), p. 81.Google Scholar
  5. 5.
    R. S. Brown and T. G. Traylor, J. Amer. Chem. Soc.,95, 8025 (1973).Google Scholar
  6. 6.
    C. F. Wilcox and H. D. Banks, J. Amer. Chem. Soc.,94, 8232 (1972).Google Scholar
  7. 7.
    P. R. Schleyer and G. W. van Dine, J. Amer. Chem. Soc.,88, 2321 (1966).Google Scholar
  8. 8.
    L. D. Kispert, C. Engelman, C. Dyas, and C. V. Pittman, J. Amer. Chem. Soc.,93, 6948 (1971).Google Scholar
  9. 9.
    J. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York-London (1972).Google Scholar
  10. 10.
    R. G. Pews and N. D. Ojha, J. Amer. Chem. Soe.,91, 5769 (1969).Google Scholar
  11. 11.
    P. H. Weiner and E. R. Malinowski, J. Phys. Chem.,71, 2791 (1967).Google Scholar
  12. 12.
    S. M. Shostakovskii, Ya. M. Kimel'fel'd, and A. V. Bobrov, Chemistry of Acetylene [in Russian], Nauka (1968), p. 267.Google Scholar
  13. 13.
    J. P. Galy, Compt. Rend. Aead. Argic. France,C275, 1531 (1972).Google Scholar
  14. 14.
    G. A. Kalabin, B. A. Trofimov, V. M. Bzhezovskii, D. F. Kushnarev, S. V. Amosova, N. S. Gusarova, and M. L. Al'pert, Izv. Akad. Nauk SSSR, Ser. Khim., 576 (1975).Google Scholar
  15. 15.
    J. T. Clerc, E. Pretseh, and S. Sternhell, C13-Kernresonanzspectroscopie, Frankfurtan-M, Acad. Verlag (1973).Google Scholar
  16. 16.
    J. B. Lambert and E. S. Maguar, Organic Magnetic Resonance,5, 403 (1973).Google Scholar
  17. 17.
    O. A. Subbotin, A. S. Kozmin, Yu. K. Grishin, N. M. Sergeyev, and I. G. Bolesov, Organic Magnetic Resonance,4, 53 (1972).Google Scholar
  18. 18.
    I. R. Ager, L. Phillips, and S. J. Roberts, J. Chem. Soc., Perkin Trans. II (1972), p. 1988.Google Scholar
  19. 19.
    S. M. Shostakovskii, A. V. Bobrov, and A. N. Velkov, Izv. Akad. Nauk SSSR, Ser. Khim., 160 (1968).Google Scholar
  20. 20.
    G. Feugeas and J. P. Calv. Compt. Rend. Aead. Agric. France,C266, 1125 (1968).Google Scholar

Copyright information

© Plenum Publishing Corporation 1976

Authors and Affiliations

  • G. A. Kalabin
    • 1
    • 2
  • D. F. Kushnarev
    • 1
    • 2
  • S. M. Shostakovskii
    • 1
    • 2
  • T. K. Voropaeva
    • 1
    • 2
  1. 1.Irkutsk Institute of Organic ChemistrySiberian Branch of the Academy of Sciences of the USSRUSSR
  2. 2.Institute of Petrochemical and Coal Tar Chemical SynthesisA. A. Zhdanov Irkutsk State UniversityUSSR

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