Skip to main content
Log in

Synthesis of 3-alkyl(aryl)thietanes

  • Published:
Petroleum Chemistry Aims and scope Submit manuscript

Abstract

A preparative procedure for the synthesis of thietanes bearing alkyl substituents in the β-position was developed. Using this procedure, 3-substituted thietanes can be obtained in four steps with an ultimate yield of > 50%. 3-R-thietanes (where R = CH3, C4H9, C5H11, C6H13, C6H5) and the corresponding sulfoxides and sulfones were synthesized and examined. The feasibility of preparation of gem-3,3-substituted thietanes was exemplified by the synthesis of 3,3-dihexylthietane.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. B. K. Clapperton, E. O. Minot, and D. R. Crump, J. Chem. Ecol. 15, 291 (1989).

    Article  CAS  Google Scholar 

  2. R. D. Adams, J. L. Perrin, J. A. Queisser, and R. D. Rogers, J. Organomet. Chem. 596, 115 (2000).

    Article  CAS  Google Scholar 

  3. N. A. Akperov, Neftepererab. Neftekhim., No. 1, 44 (2004).

  4. Y. N. Romashin, T. H. Liu, B. T. Hill, and M. S. Platz, Tetrahedron Lett. 44, 6519 (2003).

    Article  CAS  Google Scholar 

  5. W. O. Siegl and C. R. Johnson, J. Org. Chem. 35, 3657 (1970).

    Article  CAS  Google Scholar 

  6. Synthesis and Properties of Organic Sulfur Compounds, Ed. by L. I. Belen’kii (Khimiya, Moscow, 1998) [in Russian].

    Google Scholar 

  7. M. Sander, Chem. Rev. 66, 341 (1966).

    Article  CAS  Google Scholar 

  8. D. C. Dittmer and T. C. Sedergran, in Small Ring Heterocycles, Ed. by A. Hassner (Wiley, New York, 1985), Part III, p. 431.

    Google Scholar 

  9. Y. Etienne and R. Soulas, in Heterocyclic Compounds with Three and Four Membered Rings, Ed. by A. Weissberger (Wiley, New York, 1964), p. 685.

    Google Scholar 

  10. E. Block, in Comprehensive Heterocyclic Chemistry, Ed. by A. R. Katritzky (Pergamon, 1976), Vol. 7,Part 5, p. 403.

  11. N. P. Volynskii and S. E. Shevchenko, Neftekhimiya 47, 125 (2007) [Pet. Chem. 47, 109 (2007)].

    CAS  Google Scholar 

  12. N. P. Volynskii, Neftekhimiya 43, 380 (2003) [Pet. Chem. 43, 344 (2003)].

    CAS  Google Scholar 

  13. Organic Syntheses, Collective Volume 1 ed. by H. Gilman et al. (Wiley, New York, 1942; Inostrannaya Literatura, Moscow, 1949).

    Google Scholar 

  14. Properties of Organic Compounds: A Handbook, Ed. by A. A. Potekhin (Khimiya, Leningrad, 1984) [in Russian].

    Google Scholar 

  15. N. G. Gaylord, Reduction with Complex Metal Hydrides (Interscience, New York, 1956; Inostrannaya Literatura, Moscow, 1959).

    Google Scholar 

  16. N. P. Volynskii, L. I. Perepelitchenko, and L. A. Zegel’man, Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2506 (1987).

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to S. E. Shevchenko.

Additional information

Original Russian Text © S.E. Shevchenko, N.P. Volynskii, 2008, published in Neftekhimiya, 2008, Vol. 48, No. 2, pp. 123–128.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shevchenko, S.E., Volynskii, N.P. Synthesis of 3-alkyl(aryl)thietanes. Pet. Chem. 48, 123–128 (2008). https://doi.org/10.1134/S0965544108020084

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0965544108020084

Keywords

Navigation