A new direct formation of benzyllithium reagent on an insoluble polymer

  • Shinichi Itsuno
  • Koji Shimizu
  • Koichi Kamahori
  • Koichi Ito
Communication

Abstract

Hydrogen-metal exchange reactions using butyllithium have been studied on cross-linked poly(4-methylstyrene) to prepare polymer-bound benzyllithium reagent, which is a valuable starting material for functionalized resins. A simple one-step lithiation of pendant tolyl group of poly(4-methylstyrene) was achieved with a degree of lithiation as high as 50% using t-butyllithium in tetrahydrofuran.

Key words

Polymer-supported benzyllithium poly(4-methylstyrene) t-butyllithium hydrogen-metal exchange 

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References

  1. 1.
    E. C. Blossey and W. T. Ford, inComprehensive Polymer Science, G. Allen, ed. (Pergamon: Oxford, 1989), Vol. 6, p. 81; D. C. Sherrington and P. Hodge, eds.,Syntheses and Separations Using Functional Polymers, (Wiley, Chichester, 1988).Google Scholar
  2. 2.
    D. G. Darling and J. M. J. Fréchet,J. Org. Chem. 51, 2270 (1986).Google Scholar
  3. 3.
    M. Tomoi and W. T. Ford,J. Am. Chem. Soc. 103, 3821 (1981).Google Scholar
  4. 4.
    J. March,Avanced Organic Chemistry (John Wiley and Sons, New York, 1985), and references therein.Google Scholar
  5. 5.
    J. M. J. Fréchet, D. G. Darling, S. Itsuno, P.-Z. Lu, M. V. de Meftahi, and W. A. Rolls, Jr.,Pure Appl. Chem. 60, 353 (1988).Google Scholar
  6. 6.
    E. Negishi,Organometallics in Organic Synthesis (John Wiley and Sons, New York, 1980).Google Scholar
  7. 7.
    M. J. Farral and J. M. J. Fréchet,J. Org. Chem. 41, 3877 (1976).Google Scholar
  8. 8.
    S. Itsuno, D. G. Darling, H. D. H. Stöver, and J. M. J. Fréchet,J. Org. Chem. 52, 4644 (1987).Google Scholar
  9. 9.
    C. G. Screttas, J. F. Eastham, and C. W. Kamienski,Chimia 24, 109 (1970).Google Scholar
  10. 10.
    H. Gilman, H. A. Pacevitz, and O. Baine,J. Am. Chem. Soc. 62, 1514 (1940).Google Scholar
  11. 11.
    D. Seyferth and M. A. Weiner,J. Org. Chem. 24, 4797 (1959).Google Scholar
  12. 12.
    J. F. Vozza,J. Org. Chem. 24, 720 (1959).Google Scholar
  13. 13.
    S. Mahanraj and W. T. Ford,Macromolecules 19, 2470 (1986).Google Scholar
  14. 14.
    P. Hodge and D. C. Sherrington, eds.,Polymer-Supported Reactions in Organic Synthesis (John Wiley and Sons, Chichester, 1980); J. Seidl, J. Malinsky, K. Dusek, and M. Mutter,Adv. Polym. Sci. 5, 113 (1967); A. Guyot and M. Bartholin,Prog. Polym. Sci. 8, 277 (1982); R. L. Albright,React. Polym. 4, 155 (1986).Google Scholar
  15. 15.
    M. D. Rausch and A. J. Sarnelli,Adv. Chem. Ser. 130, 248 (1974).Google Scholar
  16. 16.
    G. A. Crosby and M. Kato,J. Am. Chem. Soc. 99, 278 (1977); B. J. Cohen, M. A. Kraus, and A. Patchornik,J. Am. Chem. Soc. 99, 4165 (1977); M. L. Hallensleben,Angew. Makromol. Chem. 31, 147 (1973); D. E. Bergbreiter, J. R. Blanton, and B. Chen,J. Org. Chem. 48, 5366 (1983); B. Brix and T. Clark,J. Org. Chem. 53, 3365 (1988).Google Scholar

Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • Shinichi Itsuno
    • 1
  • Koji Shimizu
    • 1
  • Koichi Kamahori
    • 1
  • Koichi Ito
    • 1
  1. 1.Department of Materials ScienceToyohashi University of TechnologyToyohashiJapan

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