Abstract
The behavior of the adducts of alicyclic epoxyenamines with sulfene under electron impact and also their 13C NMR spectra were studied. The initial fragmentation of these compounds, which takes place with the ejection of sulfene, is accompanied by a specific hydrogen rearrangement of the molecular ion. The degree of substitution of the cyclohexane ring has a significant effect on the nature of the subsequent dissociation, which leads to extensive degradation of the oxirane ring.
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I. G. Tishchenko, G. I. Polozov, and A. F. Abramov, Vestn. Belorus. Un-Ta, No. 2, 12 (1980).
B. Lamm, Acta Chem. Scand, Ser. B, 29, 332 (1975).
L. N. Koikov, P. B. Terent'ev and N. S. Kulikov, Zh. Org. Khim., 17, No. 5, 1087 (1981).
L. N. Koikov, P. B. Terent'ev, I. P. Gloriozov, V. N. Torocheshnikov, V. N. Baidin, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 5, 643 (1983).
G. I. Polozov, I. G. Tishchenko, and A. F. Abramov, Zh. Org. Khim., 16, 765 (1980).
G. Stork and I. J. Borowitz, J. Am. Chem. Soc., 84, 313 (1962).
H. J. Jacobsen, S. O. Lawesson, J. T. B. Marshall, G. Schroll, and D. H. Williams, J. Chem. Soc., No. 3. 940 (1966).
R. J. Radel, B. T. Keen, and W. W. Paudler, J. Heterocycl. Chem., 14, 1389 (1977).
A. I. Ermakov and Yu. N. Sheinker, Khim. Geterotsikl. Soedin., No. 1, 65 (1981).
D. S. Yufin, Yu. T. Struchkov, L. N. Koikov, P. B. Terentev', and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 5, 651 (1983).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 267–271, February, 1986.
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Polozov, G.I., Tishchenko, I.G. & Suboch, V.P. Mass spectra and 13C NMR spectra of the adducts of epoxyenamines with sulfene. Chem Heterocycl Compd 22, 217–221 (1986). https://doi.org/10.1007/BF00519948
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DOI: https://doi.org/10.1007/BF00519948