Advertisement

Springer Nature is making Coronavirus research free. View research | View latest news | Sign up for updates

The improved synthesis and crystal structure of 20-thiocrown-4

  • 41 Accesses

  • 1 Citations

Abstract

An improved synthesis of 20-thiocrown-4 is reported, which exploits the Kellogg method of cesium carbonate in DMF mediated macrocyclization of precondensed synthones which converge at the cycloicosane structure. The crystal structure of 20-thiocrown-4 reveals a rectangular conformation for the free ligand. Each sulfur is in onegauche and oneanti torsion angle. Four carbon positions make up the corners. There are two short sides comprised of −C−C− torsion angle sequencesg ag and two long sides (aaa, g ag+). The S−C and C−C bond distances average 1.816(2) Å and 1.523(3) Å, respectively.

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

References

  1. 1.

    S. R. Cooper and S. C. Rawle:Structure and Bonding, Vol. 72, Springer Verlag, Berlin, pp. 1–72, 1990.

  2. 2.

    S. G. Murray and F. R. Hartley:Chem. Rev. 81, 365 (1981).

  3. 3.

    R. S. Glass, G. S. Wilson, and W. N. Setzer:J. Am. Chem. Soc. 102, 5068 (1980).

  4. 4.

    J. R. Hartman, R. E. Wolf, B. M. Foxman, and S. R. Cooper:J. Am. Chem. Soc. 105, 131 (1983).

  5. 5.

    R. E. Wolf, Jr., J. R. Hartman, J. M. E. Storey, B. M. Foxman, and S. R. Cooper:J. Am. Chem. Soc. 109, 4328 (1987).

  6. 6.

    D. Sellmann, P. Lechner, M. Moll, and F. Knoch:Z. Naturforsch. 46b, 209 (1991).

  7. 7.

    D. Sellmann, P. Frank, and F. Knoch:J. Organomet. Chem. 339, 345 (1988).

  8. 8.

    S. C. Rawle, G. A. Admans, and S. R. Cooper:J. Chem. Soc., Dalton Trans. 93 (1988).

  9. 9.

    J. Buter and R. M. Kellogg:J. Chem. Soc. Commun. 466 (1980).

  10. 10.

    L. A. Ochrymowycz, C.-P. Mak, and J. D. Michna:J. Org. Chem. 39, 2079 (1974).

  11. 11.

    R. E. Wolf, J. A. R. Hartman, L. A. Ochrymowycz, and S. R. Cooper:Inorg. Synth. 25, 122 (1989).

  12. 12.

    S. G. Cho, F. R. Fronczek, W. S. Taylor, and S. F. Watkins:Acta Crystallogr. C44, 769 (1988).

  13. 13.

    G. M. Sheldrick:SHELX76, A System of Computer Programs for X-ray Structure Determination, as locally modified, University of Cambridge, England, 1976.

  14. 14.

    G. M. Sheldrick: SHELXS,Acta Cryst. A46, 467 (1990).

  15. 15.

    International Tables for X-ray Crystallography, Kynoch Press, Birmingham, England, Vol. IV, 1974, pp. 72, 99, 149. Present distributor: Kluwer Academic Publishers, Dordrecht.

Download references

Author information

Correspondence to Robin D. Rogers or Leo A. Ochrymowycz.

Additional information

Supplementary data relating to this article are deposited with the British Library as Supplementary Publication No. SUP 82147 (9 pages)

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Rogers, R.D., Henry, R.F., Ochrymowycz, L.A. et al. The improved synthesis and crystal structure of 20-thiocrown-4. J Incl Phenom Macrocycl Chem 15, 145–152 (1993). https://doi.org/10.1007/BF00710223

Download citation

Key words

  • 20-thiocrown-4
  • X-ray crystal structure
  • crown ether