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

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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.

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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)

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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).

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Key words

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