Abstract
The prototropic rearrangement of a deuterated 3-hydroxytetrahydrothiophene with a β,γ-exocyclic double bond is accompanied by deuterium migration along the double bond. Thus 4-r-benzamido-3-t-deuteroxy-3-c-deutero-2-(4-methoxycarbonylbutylidene)tetrahydrothiophene gives cis- and trans-4-r-benzamido-3-oxo-2-(4-methoxycarbonylbutyl)tetrahydro-2,4,4′-d3-thiophene, which, as a result of reduction with sodium borohydride, gives two isomers, viz., 4-r-benzamido-3-t-hydroxy-2-t- and -2-c-(4-methoxycarbonylbutyl)tetrahydrothiophenes that are deuterated in the 2, 4, and 4′ positions.
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S. D. Mikhno, T. N. Polyanskaya, and V. M. Berezovskii, Khim. Geterotsikl. Soedin., No. 2, 175 (1973).
S. A. Harris, D. E. Wolf, R. Mozingo, R. C. Anderson, G. E. Arth, N. R. Easton, D. Heyl, A. N. Wilson, and K. Folkers, J. Am. Chem. Soc., 66, 1756 (1944).
S. D. Mikhno, T. M. Filippova, N. S. Kulachkina, T. N. Polyanskaya, I. M. Kustanovich, and V. M. Berezovskii, Khim. Geterotsikl. Soedin., No. 7, 897 (1972).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1339–1342, October, 1983.
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Mikhno, S.D., Filippova, T.M., Suchkova, I.G. et al. Reductive deuteration of 4-benzamido-3-oxo-2-(4-methoxycarbonylbutylidene)tetrahydrothiophene to give the 3-deuteroxy derivative and its prototropic isomerization. Chem Heterocycl Compd 19, 1065–1067 (1983). https://doi.org/10.1007/BF00505753
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DOI: https://doi.org/10.1007/BF00505753