Abstract
3-Benzoyl-3a,4,6,6a-tetrahydrothieno[3,4-d][1,2,3]oxathiazoline 2-oxide is formed as a result of intramolecular cyclization of cis-4-benzamido-3-chlorosulfitothiophan. Only one sulfur atom — that of the sulfoxide group — is removed from the cyclization product and the analogous 3-methoxycarbonyl-3a,4,6,6a-tetrahydrothieno[3,4-d][1,2,3]oxathiazoline 2-oxide by the action of Raney nickel; the products in this case are, respectively, cis-4-benzamido-3-hydroxythiophan and 3a,4,6,6a-tetrahydrothieno]3,4-d]oxazolidone. The three-dimensional structure of 3-acyl-3a,4,4,6a-tetrahydrothieno[3,4-d][1,2,3]oxathiazoline 2-oxide was determined by 1H and 13C NMR spectroscopy. A difference between the conformational state of 3-substituted 3a,4,6,6a-tetrahydrothieno[3,4-d][1,2,3]oxathiazoline 2-oxides and 3-substituted 3a,4,6,6a-tetrahydrothieno[3,4-d]oxazolidones was established.
Similar content being viewed by others
Literature cited
S. D. Mikhno, T. M. Filippova, N. S. Kulachkina, I. G. Razumova, and V. M. Berezovskii, Khim. Geterotsikl. Soedin., No. 3, 334 (1975).
S. D. Mikhno, T. M. Filippova, N. S. Kulachkina, T. N. Polyanskaya, I. M. Kustanovich, and V. M. Berezovskii, Khim. Geterotsikl. Soedin., No. 10, 1339 (1971).
J. W. Emsley, J. Feeney, and L. Sutcliffe, High-Resolution NMR Spectroscopy, Pergamon, Oxford (1965, 1966).
T. M. Filippova, B. D. Lavrukhin, and K. I. Shmyrev, Org. Magn. Res., 6, 92 (1974).
S. D. Mikhno, T. M. Filippova, N. S. Kulachkina, I. G. Suchkova, and V. M. Berezovskii, Khim. Geterotsikl. Soedin., No. 4, 459 (1976).
R. I. Abraham and K. M. McLanchlan, Mol. Phys., 5, 195 (1962).
C. Altonan, H. J. Geise, and C. Romers, Tetrahedron, 24, 13 (1968).
S. D. Mikhno, T. M. Filippova, N. S. Kulachkina, I. G. Razumova, V. A. Zamureenko, and V. M. Berezovskii, Khim. Geterotsikl. Soedin., No. 2, 183 (1975).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 191–197, February, 1977.
Rights and permissions
About this article
Cite this article
Mikhno, S.D., Filippova, T.M., Kulachkina, N.S. et al. Synthesis, configuration, and conformation of 3-acyl derivatives of 3a,4,6,6a-tetrahydrothieno[3,4-d][1,2,3]oxathiazoline 2-oxide. Chem Heterocycl Compd 13, 153–158 (1977). https://doi.org/10.1007/BF00497866
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00497866