Skip to main content
SpringerLink
Log in

Formation of 3,5-diphenyl-2-thiabicyclo[4.4.0]dec-Δ1,6-ene under the conditions of the pummerer reaction and its structure

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The Pummerer rearrangement was investigated in the case of 3,5-diphenyl-2-thiabicyclo [4.4.0]decane S-oxide. It is shown that, of the two possible isomers, this compound forms only 3,5-diphenyl-2-thiabicyclo[4.4.0]dec-Δ1,6-ene under the conditions of the Pummerer reaction; a secondary transformation, viz., disproportionation of the latter to 3,5-diphenyl-2-thiabicyclo[4.4.0]decane and 2,4-diphenyl-5, 6-tetramethylenethiopyrylium acetate, is observed. 3,5-Diphenyl-2-thiabicyclo[4.-4.0] dec-Δ1,6-ene was subjected to an x-ray diffraction study; it was proved unambiguously that the C1=C6 double bond has a length of 1.335 Å and that the dihydrothiopyran and cyclohexene rings have a distorted half-chair conformation: the dihedral angles between the phenyl rings and the planar fragment of the heteroring are 76.8 and 93.2 °C.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

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

    Google Scholar 

  2. J. Bloch, Ann. Chim., 10, 425 (1965).

    Google Scholar 

  3. E. N. Karaulova, G. D. Gal'pern, V. D. Nikitina, I. V. Cherepanova, and L. R. Barykina, Neftekhimiya, 12, 104 (1972).

    Google Scholar 

  4. A. Smith, R. Kalish, and E. I. Smutny, Acta Crystallogr., Sect. B, 28 3494 (1972).

    Google Scholar 

  5. S. S. Shu, Acta Crystallogr., Sect. B, 29, 1690 (1973).

    Google Scholar 

  6. I. A. Gillean, III, D. W. Phelps, and A. W. Cordes, Acta Crystallogr., Sect. B, 29, 2296 (1973).

    Google Scholar 

  7. W. Klyne and V. Prelog, Experientia, 16, 523 (1960).

    Google Scholar 

  8. W. C. Hamilton, Acta Crystallogr., 18, 502 (1965).

    Google Scholar 

  9. T. V. Stolbova, S. K. Klimenko, and V. G. Kharchenko, Zh. Org. Khim., 16, No. 1, 178 (1980).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. G. Chernyshevskii Saratov State University, 410601, Saratov

    T. V. Stolbova, S. K. Klimenko, A. A. Shcherbakov, G. G. Aleksandrov, Yu. T. Struchkov & V. G. Kharchenko

  2. Institute of Heteroorganic Compounds Academy of Sciences of the USSR, 117312, Moscow

    T. V. Stolbova, S. K. Klimenko, A. A. Shcherbakov, G. G. Aleksandrov, Yu. T. Struchkov & V. G. Kharchenko

Authors
  1. T. V. Stolbova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. K. Klimenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. A. Shcherbakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. G. G. Aleksandrov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yu. T. Struchkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. V. G. Kharchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1056–1059, August, 1980.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Stolbova, T.V., Klimenko, S.K., Shcherbakov, A.A. et al. Formation of 3,5-diphenyl-2-thiabicyclo[4.4.0]dec-Δ1,6-ene under the conditions of the pummerer reaction and its structure. Chem Heterocycl Compd 16, 818–821 (1980). https://doi.org/10.1007/BF00513161

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00513161

Keywords

Search

Navigation