Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Polymer-Supported Crown Ethers(Ⅳ) Synthesis and Phase-transfer Catalytic Activity

  • Shim Jae Hu (Department of Chemical Engineering, Dongguk University) ;
  • Chung Kwang Bo (Department of Chemical Engineering, Dongguk University) ;
  • Masao Tomoi (Department of Applied Chemistry, Faculty of Engineering, Yokohama National University)
  • Published : 1992.06.20
Download PDF
⟨ Previous Next ⟩

Abstract

Immobilization method of lariat azacrown ethers, containing hydroxyl group in the side arm of crown ring, on the polymer matrix and the phase-transfer catalytic activity of thus obtained immobilized lariat azacrown ethers were studied. Polystyrene resins with crown ether structures and hydroxyl groups adjacent to the macrorings were prepared by the reaction of crosslinked polystyrene resins containing epoxy groups with monoaza-15-crown-5 or monoaza-18-crown-6. Microporous crosslinked polystyrene resins containing epoxy group for the syntheses of these immobilized lariat crown catalysts were prepared by suspension polymerization of styrene, divinylbenzene (DVB 2%) and vinylbenzylglycidyl ether. The immobilized lariat catalysts with 10-20% ring substitution exhibited maximal activity for the halogen exchange reactions of 1-bromooctane with aqueous KI or NaI under triphase heterogeneous conditions. Immobilized catalyst exhibited higher activity than corresponding catalyst without the hydroxyl group and this result was suggested that the active site have a structure in which the $K^+$ ion was bound by the cooperative coordination of the crown ring donors and the hydroxyl group in the side arm.

Keywords

References

  1. 'Polymer-supported Reactions in Organic Synthesis D. C. Sherrington;Hodge, P.(ed.);Sherrington, D.C.(ed.)
  2. Chem. Commun. v.394 M. Cinouini;S. Colonna;H. Montanari;F. Montanari;P. Tundo
  3. Angew. Chem., Int. Ed. Engl. v.18 S. L . Regen
  4. J. Org. Chem. v.46 S. L . Regen;D. Bolikal;C. Barcelon
  5. J. Chem. Soc. Chem. Comm. v.101 P. Tundo;P. Venturello
  6. Bull. Korean Chem. Soc.
  7. Makromol. Chem. Rapid Commun. v.8 M. Tomoi;H. Oda;H. Kakiuchi
  8. Anal. Chem. v.17 C. L. Ogg;W. L. Porter;C. O. Willits
  9. J. Am. Chem. Soc. v.103 M. Tomoi;W. T. Ford
  10. J. Polym. Sci. Polym. Chem. Ed. v.22 M. Tomoi;N. Yanai;S. Shiiki;H. Kakiuchi
  11. J. Am. Chem. Soc. v.69 W. S. Emerson;H. Heyd;V. E. Lucas;W. I. Lyness;G. R. Owens;R. W. Shortridge
  12. J. Org. Chem. v.26 J. G. Abramo;E. C. Chapin
  13. U. S. 3127382 Dow Chemical Company
  14. Chem. Abstr. v.61 W. N. DeLano
  15. Synthesis M. Tamura;J. Kochi
  16. Synthesis G. Mouzin;H. Cousse;J. P. Rieu;A. Duflos
  17. Makromol. Chem. v.189 M. Tomoi;H. Oda;H. Kakiuchi
  18. Yuki Gosei Kagaku Kyokai Shi v.26 S. Tanimoto;J. Horikawa;M. Okano;R. Oda
  19. Chem. Abstr. v.70 S. Tanimoto;J. Horikawa;M. Okano;R. Oda
  20. Monatsch. Chem. v.94 D. Braun;H. G. Keppler
  21. Chem. Rev. v.59 R. E. Parker;N. S. Isaacs
  22. Adv. Polym. Sci. v.55 W. T. Ford;M. Tomoi
  23. J. Polym. Sci. Polym. Chem. Ed. v.20 M. Tomoi;E. Ogawa;Y. Hosokawa;H. Kakiuchi
  24. Polymer v.28 J. Hradil;F. Svec;J. M. Frechet
  25. ACS Symposium Series No. 326, Amer. Chem. Soc. G. W. Gokel;kK. Arnold;T. Cleary;R. Friese;V. Gatto;D. Doli;C. Hamlon;M. Kim;S. Miller;M. Ouchi;I. Posey;A. Sandler;A. Viscariello;B. White;J. Wolfe;H. Yoo
  26. C. Reichaedt
  27. J. Am. Chem. Soc. v.89 C. J. Pederson

Cited by

  1. Vinylbenzylchloride (Chloromethylstyrene), Polymers, and Copolymers. Recent Reactions and Applications vol.39, pp.1, 1992, https://doi.org/10.1081/mc-100101418