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Stereochemical specificity of the palladium-catalyzed hydrogenation of cyclohexa[b]thiopyrans and their derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Conformationally and configurationally homogeneous 2α-R1-4α-R2-cis-1-thiadecalins with an equatorial orientation of the substituents attached to the C(2) and C(4) atoms were isolated as the final reduction products in the catalytic hydrogenation on palladium of 2-R1-4-R2-4H(6H)-cyclohexa[b]thiopyrans, cis-3-R1-5-R2-2-thiabicyclo[4.4.0]-δ1,6-decenes, and 2-R1-4-R2-cyclohexa[b]thiopyrylium tetrafluoroborates and trifluoroacetates. cis-3-R1-5-R2-2-Thiabicyclo[4.4.0]-δ1,6-decenes were obtained as intermediates in the incomplete reduction of 2-phenyl- and 2,4-diphenyl-4H-cyclohexa[b]thiopyrans and 2-(4-methoxyphenyl)-4-R2-cyclohexa[b]thiopyrylium salts; 2-R1-4-R2-6H-cyclohexa[b]thiopyrans undergo complete reduction of the double bonds of the heteroring. The hydrogenation products were oxidized to sulfoxides and sulfones.

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Literature Cited

  1. N. S. Smirnova, S. K. Klimenko, M. N. Berezhnaya, T. V. Stolbova, and V. G. Kharchenko, Zh. Org. Khim., 11, 440 (1975).

    Google Scholar 

  2. V. G. Kharchenko, O. A. Bozhenova, and A. D. Shebaldova, Zh. Org. Khim., No. 1, 2435 (1982).

    Google Scholar 

  3. S. K. Klimenko, T. V. Stolbova, I. Ya. Evtushenko, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 10, 1347 (1981).

    Google Scholar 

  4. T. V. Stolbova, S. K. Klimenko, A. A. Shcherbakov, G. G. Aleksandrov, Yu. T. Struchkov, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 8, 1056 (1980).

    Google Scholar 

  5. S. K. Klimenko, T. V. Stolbova, T. I. Tyrina, N. N. Sorokin, I. F. Leshcheva, N. M. Sergeev, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 7, 898 (1984).

    Google Scholar 

  6. S. K. Klimenko, T. I. Tyrina, N. N. Sorokin, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 2, 199 (1986).

    Google Scholar 

  7. S. K. Klimenko, M. N. Berezhnaya, and V. G. Kharchenko, Zh. Org. Khim., 10, 2425 (1974).

    Google Scholar 

  8. S. K. Klimenko, M. N. Berezhnaya, T. V. Stolbova, I. Ya. Evtushenko, and V. G. Kharchenko, Zh. Org. Khim., 11, 2173 (1975).

    Google Scholar 

  9. S. K. Klimenko, T. V. Stolbova, M. N. Berezhnaya, N. S. Smirnova, I. Ya. Evtushenko, and V. G. Kharchenko, Zh. Org. Khim., 10, 1942 (1974).

    Google Scholar 

  10. T. V. Stolbova, S. K. Klimenko, and V. G. Kharchenko, Zh. Org. Khim., 16, 178 (1980).

    Google Scholar 

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Authors and Affiliations

  1. N. G. Chernyshevskii Saratov State University, 410600, Saratov

    S. K. Klimenko, T. I. Tyrina & N. N. Sorokin

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  1. S. K. Klimenko
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  2. T. I. Tyrina
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  3. N. N. Sorokin
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 614–619, May, 1987.

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Klimenko, S.K., Tyrina, T.I. & Sorokin, N.N. Stereochemical specificity of the palladium-catalyzed hydrogenation of cyclohexa[b]thiopyrans and their derivatives. Chem Heterocycl Compd 23, 506–512 (1987). https://doi.org/10.1007/BF00476376

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  • DOI: https://doi.org/10.1007/BF00476376

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