Conclusions
-
1.
The existence of the dinitrate of 3,4-butanediol 1,2-oxide as a mixture of the erythro and threo isomers was confirmed on an NMR spectrometer that operated at a frequency of 200 MHz. The spectra of the individual isomers were isolated and analyzed.
-
2.
We synthesized the erythro and threo isomers of 3,4-butanediol 1,2-oxide dinitrate. A study was made of the NMR spectra of these compounds and the relation between the parameters of the spectra and the structure of the diastereomers was discussed.
-
3.
Some members of the partial nitrates of α-epoxy alcohols, namely the 4-nitrates of erythro- and threo-3,4-butanediol 1,2-oxide, were obtained for the first time.
Similar content being viewed by others
Literature cited
L. T. Eremenko and A. M. Korolev, Izv. Akad. Nauk SSSR, Ser. Khim., 449 (1969).
V. A. Zabrodin, V. E. Solov'ev, P. K. Kirillov, K. A. Tikhonov, and L. N. Gal'perin, Prib. i Tekhn. Eksperim., 158 (1970).
E. O. Bishop, Ann. Rev. NMR Spectroscopy, Vol. 1, Academic Press, New York (1968), p. 91.
C. J. MacDonald and W. F. Reynolds, Can. J. Chem.,48, 1046 (1970).
J. A. Pople, W. G. Schneider, and H. J. Bernstein, High-Resolution Nuclear Magnetic Resonance [Russian translation], IL (1962).
H. Booth, Progress in NMR Spectroscopy, Vol. 5, Pergamon Press, New York (1969), p. 149.
S. L. Spassov, Tetrahedron,25, 3631 (1969);27, 1323 (1971).
T. N. Huckerby, Ann. Reports NMR Spectroscopy, Vol. 3, Academic Press, New York (1970), p. 1.
L. T. Eremenko and A. M. Korolev, Izv. Akad. Nauk SSSR, Ser. Khim., 1436 (1966); 147 (1970).
L. T. Eremenko and A. M. Korolev, ibid.,1142, 1354 (1967); 1125 (1968); 920 (1970).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1549–1554, July, 1973.
The authors thank I. S. Krainskii for his assistance in obtaining the spectra at 200 MHz.
Rights and permissions
About this article
Cite this article
Lagodzinskaya, G.V., Zabrodin, V.A., Korolev, A.M. et al. Separation of signals and analysis of NMR spectra of type ABKPQY of a mixture of the erythro and threo isomers of 3,4-butanediol 1,2-oxide dinitrate on a spectrometer with an operating frequency of 200 MHz. Russ Chem Bull 22, 1502–1506 (1973). https://doi.org/10.1007/BF00930048
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00930048