Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Conformations of the Acyl Esters of p-Tert-butylcalix[4]arene and Calix[4]arene

  • No Kwanghyun (Department of Chemistry, Sookmyung Women's University) ;
  • Koo Hee Jung (Department of Chemistry, Sookmyung Women's University)
  • Published : 1994.06.20
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Abstract

Tetra acyl esters of p-tert-butylcalix[4]arene and calix[4]arene, including acetyl, propionyl, butyryl and isobutyryl, are synthesized and their conformations are inferred from $^1H-NMR$ and $^{13}C-NMR$ spectra. The conformer distribution is affected by the presence of t-butyl group, whereas the acylation products of p-t-butylcalix[4]arene are the cone conformers, those of calix[4]arene are mostly partial cone and/or 1,3-alternate conformers. The conformational outcome is also affected by the method of preparation, the NaH-induced reaction is prefered to the acid-induced reaction for cone and partial cone. Interestingly, 1,2-alternate conformer was isolated in 14% yield from the butyrylation of calix[4]arene.

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References

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  1. Enantiomerization Barrier of all‐cis C‐Me‐tetrahydroxy p‐tert‐butylcalix[4]arene and Atropisomeric Equilibrium of its Tetraacetoxy Derivatives vol.2020, pp.13, 1994, https://doi.org/10.1002/ejoc.202000212