Abstract
It is shown that the reaction of the four isomers of 4-methylsulfonamido-3-methylsulfonyloxy-2-(4-methoxycarbonylbutyl)tetrahydrothiophene with sodium azide leads to the formation of only a trans-3-azido-4-aminotetrahydrothiophene. Consequently, the reaction of cis-3,4-disubstituted tetrahydrothiophenes proceeds with inversion of the configuration at the C(3) atom, whereas the reaction of trans-3,4-disubstituted tetrahydrothiophenes unusually proceeds without a change in the configuration, evidently through the intermediate formation of an aziridine ring. In addition, the reaction of 4-r-methylsulfonamido-3-t-methylsulfonyloxy-2-t(or-c)-(4-methoxycarbonylbutyl)tetrahydrothiophene with sodium azide leads to migration of the amino group from the 3 position to the 4 position with inversion of the configuration and the formation of 4-r-azido-3-t-methylsulfonamido-2-c(or t)-(4-methoxycarbonylbutyl)tetrahydrothiophene.
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S. D. Mikhno, T. M. Filippova, I. G. Suchkova, and V. M. Berezovskii, Khim. Geterotsikl. Soedin., No. 10, 1339 (1983).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1343–1347, October, 1983.
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Mikhno, S.D., Filippova, T.M., Kulachkina, N.S. et al. Stereospecificity of the formation of substituted azidotetrahydrothiophenes. Chem Heterocycl Compd 19, 1068–1072 (1983). https://doi.org/10.1007/BF00505754
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DOI: https://doi.org/10.1007/BF00505754