Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Calix[4]arenes in AAAB or AABB Type Substitution at Upper Rim

  • Published : 1996.06.20
Download PDF
⟨ Previous Next ⟩

Abstract

Seven cali[4]arenes, having two different substituents in AAAB or AABB pattern at the upper rim of calix were synthesized by fragmentation condensation reaction of p-substituted phenol trimer (AAA) with 2,6-bishydroxymethylated 4-substituted phenol (B) or that of dimer (AA) with 2,2'-bishydroxymethylated dimer (BB). An equimolar mixture of the coupling components (trimer and monomer or dimer and dimer) was refluxed in dioxane in the presence of TiCl4to afford calix[4]arene 6 and 7 in 15-38% yield. The structure of calix[4]arenes was confirmed by elemental analysis and the 1H/13C NMR spectroscopy.

Keywords

References

  1. Royal Society of Chemistry Gutsche, C. D. Calixarenes;Stoddart, J. F.(ed.)
  2. A Versatile Class of macrocyclic Compounds Calixarenes;Vicens, J.(ed.);Bohmer, V.(ed.)
  3. Angew. Chem. Int. Ed. Eng. v.34 Bohmer, V.
  4. J. Chem. Soc., Chem. Commun. No, K. H.;Hong, M.
  5. Bull. Korean Chem. Chem. v.13 Hwang, K. L.;Ham, S. H.;No, K. H.
  6. J. Chem. Soc., Chem. Commun. Bohmer, V.;Merkel, L.;Kunz, U.
  7. J. Org. Chem. v.52 Bohmer, V.;marschollek, F.;Zettz, L.
  8. J. Org. Chem. v.59 Alam, I.;Sharma, S. K.;Gutsche, C. D.
  9. Supramol. Chem. v.1 Kikuchi, T.;Iki, H.;Tsuzuki, H.;Shinkai, S.
  10. Tetrahedron Ltt. v.30 van Loon, J-D.;Arduini, A.;Verboom, W.;Ungaro, R.;van Hummel, G.J.;Harkema, S.;Reinhoudt, D. N.
  11. J. Org. Chem. v.55 van Loon,J-D.;Arduini, A.;Coppi, L.;Verboom, W.;Pochini, A.;Ungaro, R.;Harkema, S.;Reinhoudt, D. N.
  12. Synthesis Timmerman, P.;Verboom, W.;Reinhoudt, D. N.;Arduini, A.;Grandi, S.;Sicuri, A. R.;Pochini, A.;Ungaro, R.
  13. J. Org. Chem. v.47 No, K. H.;Gutsche, C. D.
  14. J. Am. Chem. Soc. v.110 Goldmann, H.;Vogt, W.;Paulus, E.;Bohmer, V.
  15. J. Org. Chem. v.58 Andreetti, G. D.;B hmer, V.;Jordon, J. D.;Tabatabai, M.;Ugozzoli.;Vogt, W.;Wolff, A.
  16. J. Prakt. Chem. v.153 Hanus, F.;Fuch, E.
  17. J. U. S. Pat. 4, 259, 464 Buriks, R. S.;Faube, A. R.;Munch,
  18. J. Org. Chem. v.43 Still, W. C.;Kahn, m.;Mitra, M.
  19. Bull Korean Chem. Soc. v.14 No, K. H.;Hwang, K. L.
  20. Angew. Chem. v.46 Koebner, M.