Synthesis of insoluble polymer-supported thiazoles and use of 2-methyl-4-poly(styrylmethyl)thiazolium hydrotribromide as a new brominating reagent

European Polymer Journal

Volumn 32, Issue 2, 1996, Pages 193-199

  Kessat, Ahmed ^a   Babadjamian, André ^a  

^a Ecole Centrale Marseille   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION AGENT; ARALKYLATION; BROMINATION; CROSSLINKED COPOLYMER; EXPERIMENTAL STUDY; IMINIUM COMPOUNDS; LATERAL GROUP; REACTIVITY; SELECTIVITY; STYRENE COPOLYMER; THIAZOLE DERIVATIVES;

CHEMICAL MODIFICATION;

EID: 0011217143     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/0014-3057(95)00109-3     Document Type: Article

References (53)

1. R. B. Merrifield, J. Am. Chem. Soc. 85, 2149 (1963).
2. (a) N. K. Mathur, C. K. Narang and R. E. Williams. Polymers as Aids in Organic Chemistry, Academic Press, New York (1980);
3. (b) C. E. Carraher and J. A. Moore. Modifications of Polymers, Plenum Press, New York (1983);
4. (c) C. U. Pittman. In Polymer-Supported Reactions in Organic Synthesis (edited by P. Hodge and D. C. Sherrington), Wiley, New York (1980);
5. (d) J. Lieto, D. Milstein, J. V. Minkiewicz and B. C. Gates. A.C.S., Advanced Series, New York (1982);
6. (e) J. Lieto, D. Milstein, J. V. Minkiewicz, B. C. Gates and R. L. Albright. CHEMTECH p. 46 (1983);
7. (f) G. Gelbard. Actualité chimique 7, (1984).
8. (a) Y. Marcus and A. S. Kertes. Ion Exchange and Solvent Extraction of Metal Complexes, Wiley, New York (1969);
9. (b) J. M. J. Fréchet and M. J. Farrall. Chemistry and Properties of Cross-linked Polymers (edited by S. S. Labana), Academic Press, New York (1977);
10. W. T. Ford. Polymeric Reagents and Catalyst, American Chemical Society, Washington, D.C. (1986);
11. P. Laszlo. Preparative Chemistry Using Supported Reagents, Academic Press, San Diego (1987);
12. (e) P. Hodge and D. C. Sherrington. Syntheses and Separations Using Functional Polymers, Wiley, Chichester (1988);
13. (f) J. L. Benham and J. F. Kinsle. Chemical Reactions on Polymers, American Chemical Society, Washington, D.C. (1988).
14. C. L. Schilling Jr. and J. E. Mulvaney. Macromolecules 1, 452 (1968)
15. and D. R. Stevenson, Chem. Abstr. 77, 35025d (1972).
16. J. Castells, E. Dunanch, F. Geijo, F. Pujol and P. M. Segura. Israel J. Chem. 17, 278 (1978).
17. K. Karimian, F. Mohanazadeh and S. Rezai. J. Heterocyclic Chem. 20, 1119 (1983).
18. (a) J. V. Metzger. Thiazole and Its Derivatives, Wiley, New York (1979);
19. (b) J. V. Metzger. Thiazoles and Their Benzo Derivatives In Comprehensive Heterocyclic Chemistry (edited by A. R. Kartritzky and C. W. Rees), Pergamon Press, Oxford (1984).
20. (a) H. O. House. Modern Synthetic Reactions, 2nd edn, p. 477. Benjamin, New York (1972);
21. (b) N. De Kempe and R. Verhé. The Chemistry of α-Haloketones, α-Haloaldehyde and α-Haloimides (edited by S. Patai and Z. Rappoport), Wiley, New York (1988);
22. (c) J. March. Advanced Organic Chemistry, 4th edn, p. 587, Wiley, New York (1992).
23. (a) L. Forlani and A. Medici. J. Chem. Soc. Perkin Trans. 1, 1169 (1978);
24. (b) L. Forlani, M. Magagni and P. E. Todesco, Gazz. Chim. Ital. 109, 377 (1979);
25. (c) L. Forlani. Synth. Commun. pp 487 (1980).
26. F. E. Hooper and T. B. Johnson. J. Am. Soc. Chem. 56, 470 (1943).
27. J. M. J. Fréchet, M. D. Smet and M. J. Farrall. J. Org. Chem. 44, 1774 (1979).
28. Microanalyses were carried out in the Service Central d'Analyses (CNRS), Vernaison, France.
29. 3 were purchased from Fluka (see Experimental Section, preparation of II).
30. L. Galeazzi. Ger. Offen. 2, 455,946 (1975).
31. K. W. Pepper, H. M. Paisley and M. A. Young. J. Chem. Soc. pp. 4097 (1953) and Ref. [2(d and e)].
32. The durations of these different operations have not been optimized.
33. The effective bromine content corresponds to the quantity introduced only during the hydrotribromination processes; the remaining bromine of I, II and III after the functionalization steps (Table 1) has been obviously deduced from its total amount.
34. S. Kajigaeshi and T. Kakinami. Yuki Gosei Kagaku Kyokaishi 46, 986 (1988).
35. M. Finkelstein, S. A. Hart, W. M. Moore and D. Ross. J. Org. Chem. 51, 3548 (1986).
36. J. R. Catch and D. F. Elliott. J. Chem. Soc. p. 279 (1948).
37. V. Calo, L. Lopez and G. Pesce. J. Chem. Soc., Perkin Trans. 15, 501 (1977).
38. A. Akelah, M. Hassanein and F. Abdel-Galil. Eur. Polym. J. 20, 221 (1984).
39. G. A. Olah, Y. D. Vakar and M. Arvanaghi. Tetrahedron Lett. 3653 (1979).
40. S. Magen, J. Oren and B. Fuchs, Tetrahedron Lett. 25, 3369 (1984).
41. M. Zupan and B. Sket. Synth. Commun. 19, 2481 (1989).
42. J. Berthelot, C. Guette, P. L. Desbène, J. J. Basselier, P. Chaquin and D. Masure. Can. J. Chem. 68, 464 (1990).
43. H. A. Muathen. J. Org. Chem. 57, 2740 (1992).
44. M. M. Aly, R. Bolton and G. H. Williams. J. Chem. Res. S p. 24 (1983).
45. P. Mencarelli and I. Stegel. Gazz. Chim. Ital. 117, 83 (1987).
46. C. Yaroslavsky, A. Patchornic and E. Katchalski. Tetrahedron Lett. 42, 3629 (1970).
47. M. Okawara and H. Shinokara. Kogyo Kagaku Zasshi 60, 75 (1957);
48. Chem. Abstr. 53, 5730h (1957).
49. Y. Yanagisawa, M. Akiyama and M. Okawara. Kogyo Kagaku Zasshi 72, 1399 (1969);
50. Chem. Abstr. 71, 113,410 (1969).
51. B. Sket and M. Zupan. J. Org. Chem. 51, 929 (1986).
52. A. Akelah, A. Selim and H. El-Hamshary. Eur. Polym. J. 24, 1111 (1988).
53. M. Hassanein, A. Akelah and H. El-Hamshary. Eur. Polym. J. 25, 1083 (1989).