Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and X-ray Crystallographic Characterization of p-Diacetylcalix[4]arene

  • Young Ja Park (Department of Chemistry, Sook Myung Women's University) ;
  • Kwanghyun No (Department of Chemistry, Sook Myung Women's University) ;
  • Jung Mi Shin (Department of Chemistry, Sook Myung Women's University)
  • Published : 1991.10.20
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Abstract

A simple route is described for the selective functionalization of calixarene at the para positions of phenyl rings. Calix[4]arene tetraacetate 2, obtained from the treatment of calix[4]arene with acetic anhydride, undergoes Fries rearrangement to yield the diametrically para substituted p-diacetylcalix[4]arene 3 in 80% yield. The crystal and molecular strucutre has been determined by X-ray diffraction method. The crystals are orthorhombic, space group Pna21, with a = 11.121 (3), b = 10.374 (3), c = 21.690 (6) $\AA$ and Z = 4. The structure was solved by direct method and refined by full-matrix least-squares methods to final R of 0.036 for 1795 observed reflections. Each hydroxyl hydrogen atom is disordered over two positions. The macrocycle exists in the cone conformation which is determined by the strong circular intramolecular flip-flop type hydrogen bonds of phenolic OH, while crystal packing effects of the diametrically para-acetyl substituents seem to be responsible for the distortion of the cone conformation.

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References

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