The Invention of Radical Chain Reactions of Value in Organic Synthesis

  • Francesco Minisci
Part of the NATO ASI Series book series (NSSA, volume 197)


The title of this lecture was suggested by Professor Barton, who has brought a very relevant contribution to the organic synthesis by this approach, particularly with sulphur derivatives and, in fact, should have been the lecturer on this subject. Since Professor Barton, unfortunately, was unable to participate at this meeting, I have the ungrateful task to substitute for such a scientific master. Maintaining just the title is, however, easier since it covers also my own research activities.


Alkyl Radical Chain Process Hydrogen Abstraction Diazonium Salt Radical Chain Reaction 


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  1. 1.
    R. Leuckart, J. Prakt. Chem. 41: 187 (1890).Google Scholar
  2. 2.
    L. Landsberg, Chem. Ber. 23. I: 454 (1890).Google Scholar
  3. 3.
    F. Minisci, Ital. Pat. 580012 (17/5/1957); Angew. Chem. 70:599 (1958); Gazz. Chico. Ital. 89:626 (1958), 90: 2439 (1959).Google Scholar
  4. 3.
    F. Minisci, Angew. Chem. 70:599 (1958)Google Scholar
  5. F. Minisci, Gazz. Chico. Ital. 89:626 (1958), 90: 2439 (1959).Google Scholar
  6. 4.
    R.M. Wilson and S.W. Wunderly, J. Am. Chem. Soc. 96: 7350 (1974).CrossRefGoogle Scholar
  7. 5.
    a. P. Bongeard, M.D. Johnson, and G. Lampan, J. Chem. Soc., Perkin Trans. I. 849 (1982)Google Scholar
  8. M.R. Ascheroft, P. Bongeard, A. Burry, C.J. Cooksey, M.D. Johnson, J.M. Hungerford, and G.M. Lampman, J. Org. Chem. 49: 1751 (1984);Google Scholar
  9. c. V.F. Patel and G. Pattenden, Tetrahedron Lett. 28: 145 (1987).Google Scholar
  10. 6.
    D.H.R. Barton, B. Lacher, B. Misterkiewiez, and S.Z. Zard, Tetrahedron 44: 1153 (1988).CrossRefGoogle Scholar
  11. 7.
    A. Good and J.C.J. Thynne, Trans. Farad. Soc. 63: 2708, 2720 (1967).CrossRefGoogle Scholar
  12. F. Minisci, Gazz. Chim. Ital. 89:1910, 1922, 1941, 2428 (1959); 90:1307 (1960); Rend. Accad. Lincei 8 24:538 (1958); Acc. Chem. Res. 8:165 (1975).Google Scholar
  13. 9.
    W.A. Waters, J. Chem. Soc. 266 (1942).Google Scholar
  14. 10a.
    B. Giese, “Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds”, J.E. Baldwin, ed., Pergamon Press, Oxford (1986).Google Scholar
  15. Free Radicals in Synthesis and Biology“, F. Minisci, ed., Kluwer Acad. Publ., Dordrecht (1989).Google Scholar
  16. 11.
    E. Minisci, E. Vismara, and F. FontanaGoogle Scholar
  17. Tetrahedron Letters 28:6373 (1987), 29:1975 (1988); ref. 10b, p. 53.Google Scholar
  18. Paramagnetic Organometallic Species in Activation, Selectivity, Catalysis”, M. Chanon, ed., Kluwer Acad. Publ., Dordrecht, pp. 29 (1989).Google Scholar
  19. 12.
    D. Veltwisch, E. Janata, and K.-D. Asmus, J. Chem. Soc., Perkin Trans. 2 146 (1980).CrossRefGoogle Scholar
  20. 13.
    B.C. Gilbert, R.O.C. Norman, and R.C. Sealy, J. Chem. Soc., Perkin Trans. 2 303 (1975).CrossRefGoogle Scholar
  21. 14.
    K.-D. Asmus, E. Anklam, and H. Mohan, in “Proceeding of the Fifth International Symposium on Organic Free Radicals”, H. Fischer, ed., Springer Verlag, pp. 3 and references therein (1988).Google Scholar
  22. 15.
    J.A. Hawari, J.M. Kanabus-Kaminska, D.D. Wayner and D. Griller, “Substituent Effects in Radical Chemistry”, H.G. Viehe, ed., D. Reidel Publ. Co., Dordrecht, pp. 81 (1986).Google Scholar
  23. 16.
    F. Minisci, E. Vismara, and F. Fontana, Heterocycles 28: 489 (1989).CrossRefGoogle Scholar
  24. 17a.
    D.H.R. Barton and S.Z. Zard, Pure and Appl. Chem. 58:675 (1986); ref. 15, p. 443, b. D.H.R. Barton and N. Ozbalik, ref. 11b, p. 1.Google Scholar
  25. 18a.
    J.C. Scaiano and K.U. Ingold, J. Am. Chem. Soc. 98: 4727 (1976);CrossRefGoogle Scholar
  26. b. J.C. Scaiano, J.P. Tremblay, and K.U. Ingold, Can. J. Chem. 54: 3407 (1976)CrossRefGoogle Scholar
  27. D. Forrest, K.U. Ingold, and D.H.R. Barton, J. Phys. Chem. 81: 915 (1977)CrossRefGoogle Scholar
  28. D. Forrest and K.U. Ingold, J. Am. Chem. Soc. 100: 3868 (1978).CrossRefGoogle Scholar
  29. 19.
    M. Newcomb and J. Kaplan, Tetrahedron Lett. 28: 1615 (1987).CrossRefGoogle Scholar
  30. 20.
    D.H.R. Barton, N. Ozbalik, and B. Vacher, Tetrahedron 44: 3501 (1988).CrossRefGoogle Scholar
  31. 21.
    D.H.R. Barton, A. Gateau-Olesker, S.D. Gero, B. Lacher, C. Tachdjian, and S.Z. Zard, J. Chem. Soc., Chem. Commun. 1790 (1987).Google Scholar
  32. D.H.R. Barton, S.D. Gero, B. Quillet-Sire, and M. Somadi, J. Chem. Soc., Chem. Commun.1372 (1988).Google Scholar
  33. 23.
    M. Newcomb and T.M. Deeb, J. Am. Chem. Soc. 109: 3163 (1987).CrossRefGoogle Scholar
  34. 24.
    F. Minisci, ref. 15, p. 391.Google Scholar
  35. 25.
    S. Auricchio, M. Bianca, A. Citterio, F. Minisci, and S. Ventura, Tetrahedron Lett. 3373 (1984).Google Scholar
  36. 26.
    A.L.J. Beckwith and B.P. Hay, J. Am. Chem. Soc. 110: 4415 (1988).CrossRefGoogle Scholar
  37. 27a.
    D.H.R. Barton and S.W. McCombie, J. Chem. Soc., Perkin Trans. 1 1574 (1975);Google Scholar
  38. b. D.H.R. Barton, D. Crick, A. Löbberding, and S.Z. Zard, J. Chem. Soc., Chem. Commun. 646 (1985); Tetrahedron 42: 2329 (1986).CrossRefGoogle Scholar
  39. 28.
    W. Hartwig, Tetrahedron 39: 2609 (1983).CrossRefGoogle Scholar
  40. 29.
    P.J. Barker and A.L.J. Beckwith, J. Chem. Soc., Chem. Commun. 683 (1984).Google Scholar
  41. 30.
    M.D. Bachi and E. Bosch, J. Chem. Soc., Perkin Trans. 1 1517 (1988).Google Scholar
  42. 31.
    D. Crich, Tetrahedron Lett. 29: 5805 (1988).CrossRefGoogle Scholar
  43. P. Delduc, C. Tailham, and S.Z. Zard, J. Chem. Soc., Chem. Commun. 308 (1988), ref. 10b, p. 263.Google Scholar

Copyright information

© Plenum Press, New York 1990

Authors and Affiliations

  • Francesco Minisci
    • 1
  1. 1.Dipartimento di ChimicaPolitecnico di MilanoMilanoItaly

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