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Study of the stereospecificity of the reaction of r-4-benzamido-t-3-hydroxy-c(or t)-2-(4-methoxycarbonylbutyl)thiophan with thionyl chloride

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It has been established that the presence of a substituent in the 2 position in trans-4-benza-mido-3-hydroxythiophan changes the mechanism of the reaction with thionyl chloride from SN2 to SN1. r-4 Benzamido-t-3-chloro-c(or t)-2- (4-methoxycarbonylbutyl)thiophan and 2-phenyl-cis (or trans)-6-(4-methoxycarbonylbutyl)-cis-3a,4,6,6a-tetrahydrothieno[3,4-d]oxazoline are formed simultaneously from r-4-benzamido-t-3-hydroxy-c(or t)-2-(4-methoxy-carbonylbutyl) thiophans on reaction with thionyl chloride. The configurations of the products were established by PMR spectroscopy by means of the temperature dependence of the vicinal spin-spin coupling constants and the angular dependence of these constants.

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Authors and Affiliations

  1. All-Union Scientific-Research Vitamin Institute, Moscow

    S. D. Mikhno, T. M. Filippova, N. S. Kulachkina, I. G. Suchkova & V. M. Berezovskli

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  1. S. D. Mikhno
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  2. T. M. Filippova
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  3. N. S. Kulachkina
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  4. I. G. Suchkova
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  5. V. M. Berezovskli
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 331–337, March, 1976.

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Mikhno, S.D., Filippova, T.M., Kulachkina, N.S. et al. Study of the stereospecificity of the reaction of r-4-benzamido-t-3-hydroxy-c(or t)-2-(4-methoxycarbonylbutyl)thiophan with thionyl chloride. Chem Heterocycl Compd 12, 282–287 (1976). https://doi.org/10.1007/BF00479564

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  • DOI: https://doi.org/10.1007/BF00479564

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