Abstract
The 1H and 13C NMR spectra of 2,5-dimethyl-4-methylene-1,3-oxathiolane were analyzed by comparison of the calculated and experimental parameters with the aid of a paramagnetic shift reagent. The data obtained from the NMR spectra were used for the establishment of the structures of the products of isomerization and alcoholysis of 2,5-dimethyl-4-methylene-1,3-oxathiolane.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
R. J. Abraham and H. J. Bernstein, Can. J. Chem., 39, 216 (1961).
M. Jackman and S. Sternhell, Application of NMR Spectroscopy in Organic Chemistry, Oxford (1968), p. 304.
U. E. Matter, C. Pascual, E. Pretsch, A. Pross, W. Simon, and S. Sternhell, Tetrahedron, 25, 691 (1969).
C. Pascual, J. Meier, and W. Simon, Helv. Chim. Acta, 49, 164 (1966).
T. F. Page, T. Alger, and D. M. Grant, J. Amer. Chem. Soc., 87, 5333 (1965).
G. C. Levy and G. L. Nelson, Carbon-13 Nuclear Magnetic Resonance for Organic Chemistry, New York (1972), p. 97.
A. S. Atavin, A. N. Mirskova, T. S. Proskurina, V. K. Voronov, and G. A. Kalabin, Khim. Geterotsikl. Soedin., 446 (1973).
G. A. Kalabin, Master's Dissertation, Irkutsk (1971), p. 127.
D. E. Dorman, M. Jautelat, and J. D. Roberts, J. Org. Chem., 36, 2757 (1971).
G. E. Maciel and G. B. Savitsky, J. Phys. Chem., 69, 3925 (1965).
D. M. Grant and E. G. Paul, J. Amer. Chem. Soc., 86, 2984 (1964).
J. T. Clerc, E. Pretsch, and S. Sternhell, 13C-Kernresonanz — Spektroskopie, Frankfurt am Mein, (1973).
T. D. Inch and N. Williams, J. Chem. Soc., C, 263 (1970).
T. D. Inch, in: Annual Reviews of NMR Spectroscopy, Vol. 2 (1969), p. 50.
S. Sternhell, Quart. Rev., 23, 236 (1969).
M. Christl, H. J. Reich, and J. D. Roberts, J. Amer. Chem. Soc., 93, 3463 (1971).
D. M. Grant and B. V. Cheney, J. Amer. Chem. Soc., 89, 5315 (1967).
C. C. Hinckley, J. Amer. Chem. Soc., 91, 5160 (1969).
B. Bleany, J. Magn. Resonance, 8, 91 (1972).
H. M. McConnell and R. E. Robertson, J. Chem. Phys., 29, 1361 (1958).
S. Farid, A. Ateya, and M. Maggio, Chem. Commun., 1285 (1971).
L. Pauling, Nature of the Chemical Bond, Cornell University Press, Ithaca, New York (1960).
D. R. Crump, J. K. M. Sanders, and D. H. Williams, Tetrahedron Lett., 4949 (1970).
B. A. Trofimov, N. I. Shergina, É. I. Kositsyna, E. P. Vyalykh, S. V. Amosova, N. K. Gusarova, and M. G. Voronkov, Reakts. Sposobnost' Organ. Soedin., 10, 757 (1973).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 606–611, May, 1975
Rights and permissions
About this article
Cite this article
Kalabin, G.A., Trofimov, B.A., Amosova, S.V. et al. Analysis of the structure of 2,5-dimethyl-4-methylene-1, 3-oxathiolane by NMR spectroscopic methods. Chem Heterocycl Compd 11, 529–533 (1975). https://doi.org/10.1007/BF00480471
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00480471