View PDF Version
 
DOI: 10.1039/A808222G (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 137-142

Preparation and reactivity of a non-styrenic polymer-supported organotin chloride catalyst

(Note: The full text of this document is currently only available in the PDF Version )

Alexandre Chemin, Hervé Deleuze and Bernard Maillard

Abstract

A new type of macroporous polymer-supported organotin hydride has been prepared by suspension copolymerisation of an allyl ether monomer bearing an organotin moiety with N-phenylmaleimide and 1,1′-(methylenedi-4,1-phenylene)bismaleimide. Several resins were synthesised using different ratios of toluene–N-methylformanilide as the porogen. The swelling characteristics of the resins in different solvents and their specific surface areas were estimated. The organotin chloride-functionalised beads obtained showed good activity and good stability to reduction of bromoadamantane by sodium borohydride. Tin leaching during successive reuses was estimated.

References

  1. A. Chemin, H. Deleuze and B. Maillard, Eur. Polym. J., 1998, 34, 1395 CrossRef CAS.
  2. O. Morija, Y. Uruta and T. Endo, J. Polym. Sci., Part A: Polym. Chem. Ed., 1991, 29, 1501 CrossRef.
  3. R. Z. Greenley, Free radical copolymerization reactivity ratio, in Polymer Handbook, ed. J. Brandrup and E. H. Immergut, Wiley, New York, 3rd edn., 1989 Search PubMed.
  4. J. M. G. Cowie, in Comprehensive Polymer Science, ed. G. W. Allen and J. C. Beringlon, Pergamon Press, Oxford, 1989, vol. 4, ch. 22, p. 377 Search PubMed.
  5. B. Boutevin and A. El Bachiri, Eur. Polym. J., 1995, 31, 321 CrossRef CAS.
  6. H. Jacobelli, M. Bartholin and A. Guyot, J. Appl. Polm. Sci., 1979, 23, 927 Search PubMed.
  7. T. Matynia, B. Gawdzik and E. Chmielewska, J. Appl. Polm. Sci., 1996, 60, 1971 Search PubMed.
  8. D. C. Sherrington, Chem. Commun., 1998, 2275 RSC.
  9. F. M. B. Coutinho and D. Rabelo, Eur. Polym. J., 1992, 28, 1553 CAS.
  10. A. Guyot, in Synthesis and Separation of Functional Polymers, ed. D. C. Sherrington and P. Hodge, Wiley, New York, 1988 Search PubMed.
  11. W. Rollo, F. Svec and J. M. J. Frechet, Polymer, 1990, 31, 165 CrossRef.
  12. P. J. Comina, A. K. Beck and D. Seebach, Org. Proc. Res. Dev., 1998, 2, 18 Search PubMed.
  13. R. A. Houghten, Proc. Natl. Acad. Sci. USA, 1985, 82, 5131 CAS.
  14. G. Dumartin, M. Pourcel, B. Delmond, O. Donard and M. Pereyre, Tetrahedron Lett., 1998, 39, 4663 CrossRef CAS.
  15. Chemistry of Waste Minimizations, ed. J. H. Clark, Blackie, Glasgow, 1995 Search PubMed.
  16. W. M. R. Dirksc, R. Lobinski and F. Adams, Anal. Sci., 1993, 9, 273 CAS.
  17. D. C. Sherrington, in Polymer-Supported Reactions in Organic Synthesis, ed. D. C. Sherrington and P. Hodge, Wiley, New York, 1980 Search PubMed.