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Neighboring Group Participation: General Principles and Application to Sulfur-Centered Reactive Species

  • Richard S. Glass
Part of the NATO ASI Series book series (NSSA, volume 197)

Abstract

There are many ways in which a substituent can affect the reactivity of a functional group, such as electronic effects (resonance, hyperconjugation, inductive, and field effects), steric effects, conformational effects, and neighboring group participation. This review focuses on one of these ways: neighboring group participation.1

Keywords

Group Participation Sulfonium Salt Neighboring Group Participation Thioether Sulfur Vibrational Freedom 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    B. Capon and S.P. McManus, in: “Neighboring Group Participation”, Vol. 1, Plenum, New York (1976).Google Scholar
  2. 2.
    M.I. Page, Chem. Soc. Rev. 2: 295 (1973).CrossRefGoogle Scholar
  3. 3.
    F.M. Menger, Acc. Chem. Res. 18: 128 (1985).CrossRefGoogle Scholar
  4. 4.
    a. A.E. Dorigo and K.N. Houk, J. Am. Chem. Soc. 109: 3698 (1987).CrossRefGoogle Scholar
  5. b. F.M. Menger and M.J. Sherrod, J. Chem. Soc. Perkin Trans. 2 1509 (1988).Google Scholar
  6. c. A.E. Dorigo and K.N. Houk, J. Org . Chem. 53: 1650 (1988).CrossRefGoogle Scholar
  7. 5.
    J.E. Baldwin, J. Chem. Soc. Chem. Commun. 734 (1976).Google Scholar
  8. 6.
    E. Block, in: “Reactions of Organosulfur Compounds”, Chp. 4, Academic Press, New York (1978).Google Scholar
  9. 7.
    E.N. Rengevich, V.I. Staninets, and E.A. Shilov, Dokl. Akad. Nauk SSSR (Engl. Trans.) 146: 787 (1962).Google Scholar
  10. 8.
    R.G. Bernett, J.T. Doi, and W.K. Musker, J. Org . Chem. 50: 2048 (1985).CrossRefGoogle Scholar
  11. 9.
    J.C. Martin, ACS Symp. Ser. 69:71 (1978).Google Scholar
  12. 10.
    C.W. Perkins, J.C. Martin, A.J. Arduengo, W. Lau, A. Alegria, and J.K. Kochi, J. Am. Chem. Soc. 102: 7753 (1980).CrossRefGoogle Scholar
  13. 11.
    T. Lavine, J. Biol. Chem. 151:281 (1943); S. Mann, Z. Anal. Chem. 173:112 (1960); K.-H. Gensch and T. Higuchi, J. Pharm. Sci. 56: 177 (1967).CrossRefGoogle Scholar
  14. 12.
    R.S. Glass and J.R. Duchek, J. Am. Chem. Soc. 98:965 (1979); D.O. Lambeth and D.W. Swank, J. Org . Chem. 44: 2632 (1976).Google Scholar
  15. 13.
    P.R. Young and L.-S. Hsieh, J. Am. Chem. Soc. 100: 7121 (1978).CrossRefGoogle Scholar
  16. 14.
    a. J.T. Doi, W.K. Musker, D.L. deLeeuw, and A.S. Hirschon, J. Org . Chem. 46: 1239 (1981).CrossRefGoogle Scholar
  17. b. A.S. Hirschon, M.M. Olmstead, J.T. Doi, and W.K. Musker, Tetrahedron Lett. 23: 317 (1982).CrossRefGoogle Scholar
  18. c. D.L. deLeeuw, M.H. Goodrow, M.M. Olmstead, W.K. Musker, and J.T. Doi, J. Org . Chem. 48: 2371 (1983).CrossRefGoogle Scholar
  19. 15.
    J.T. Doi and W.K. Musker, J.Am.Chem.Soc. 103: 1159 (1981).Google Scholar
  20. 16.
    K.A. Williams, J.T. Doi, and W.K. Musker, J. Org . Chem. 50: 4 (1985).CrossRefGoogle Scholar
  21. 17.
    J.T. Doi, P.K. Bharadwaj, and W.K. Musker, J. Org . Chem. 52: 2581 (1987).CrossRefGoogle Scholar
  22. 18.
    J. Klein and H. Stoller, Tetrahedron 30: 2541 (1974).CrossRefGoogle Scholar
  23. 19.
    A.S. Hirschon, J.D. Beller, M.M. Olmstead, J.T. Doi, and W.K. Musker, Tetrahedron Lett. 22: 1195 (1981).Google Scholar
  24. 20.
    R.S. Glass, A. Petsom, M. Hojjatie, B.R. Coleman, J.R. Duchek, J. Klug, and G.S. Wilson, J. Am. Chem. Soc. 110: 4772 (1988).CrossRefGoogle Scholar
  25. 21.
    L.A. Paquette and M.K. Scott, J. Am. Chem. Soc. 94: 6760 (1972).CrossRefGoogle Scholar
  26. 22.
    W. Tagaki, M. Ochiai, and S. Oae, Tetrahedron Lett. 6131 (1968).Google Scholar
  27. 23.
    T. Higuchi and K.-H. Gensch, J. Am. Chem. Soc. 88:5486 (1966); K.-H. Gensch, I.H. Petman, and T. Higuchi, ibid 90:2096 (1968); P.R. Young and L.-S. Hsieh, ibid 104: 1612 (1982).Google Scholar
  28. K.-H. Gensch, I.H. Petman, and T. Higuchi, ibid 90:2096 (1968)Google Scholar
  29. P.R. Young and L.-S. Hsieh, ibid 104: 1612 (1982).Google Scholar
  30. T. Higuchi and K.-H. Gensch, J. Am. Chem. Soc. 88:5486 (1966); K.-H. Gensch, I.H. Petman, and T. Higuchi, ibid 90:2096 (1968); P.R. Young and L.-S. Hsieh, ibid 104: 1612 (1982).Google Scholar
  31. 24.
    P.R. Young and M. Till, J. Org . Chem. 47: 1416 (1982).CrossRefGoogle Scholar
  32. 25.
    P.R. Young and L.-S. Hsieh, J. Org . Chem. 47: 1419 (1982).CrossRefGoogle Scholar
  33. 26.
    J.T. Doi, M.H. Goodrow, and W.K. Musker,J. Org. Chem. 51: 1026 (1986).CrossRefGoogle Scholar
  34. 27.
    H. Fujihara, R. Akaishi, and N. Furukawa, J. Chem. Soc. Chem. Commun. 930 (1987); F. Iwasaki, N. Toyoda, R. Akaischi, H. Fujihara, and N. Furukawa, Bull. Chem. Soc. Jpn. 61: 2563 (1988).CrossRefGoogle Scholar
  35. 28.
    J.T. Doi and W.K. Musker, J. Am. Chem. Soc. 100: 3533 (1978).CrossRefGoogle Scholar
  36. 29.
    K.-D. Asmus, M. Göbl, K.-O. Hiller, S. Mahling, and J. Mönig, J. Chem. Soc. Perkin Trans. 2 641 (1985).Google Scholar
  37. 30.
    W.K. Musker, P.S. Surdhar, R. Ahmad, and D.A. Armstrong, Can. J. Chem. 62: 1874 (1984).CrossRefGoogle Scholar
  38. 31.
    a. W.K. Musker, A.S. Hirschon, and J.T. Doi, J. Am. Chem. Soc. 100:7754 (1978). b. W.K. Musker, Acc. Chem. Res. 13: 200 (1980).CrossRefGoogle Scholar
  39. 32.
    a. R.S. Glass, M. Hojjatie, G.S. Wilson, S. Mahling, M. Göbl, and K.-D. Asmus, J. Am. Chem. Soc. 106: 5382 (1984).CrossRefGoogle Scholar
  40. b. S. Mahling, K.-D. Asmus, R.S. Glass, M. Hojjatie, and G.S. Wilson, J. Org . Chem. 52: 3717 (1987).CrossRefGoogle Scholar
  41. 33.
    M.J. Davies, B.C. Gilbert, and R.O.C. Norman, J. Chem. Soc. Perkin Trans. 2 731 (1983).Google Scholar
  42. 34.
    K.-D. Asmus, Acc. Chem. Res. 12: 436 (1979).CrossRefGoogle Scholar
  43. 35.
    T.G. Brown, A.S. Hirschon, and W.K. Musker, J. Phys. Chem. 85: 3767 (1981).CrossRefGoogle Scholar
  44. 36.
    G.S. Wilson, D.D. Swanson, J.T. Klug, R.S. Glass, M.D. Ryan, and W.K. Musker, J. Am. Chem. Soc. 101:1040 (1979); M.D. Ryan, D.D. Swanson, R.S. Glass, and G.S. Wilson, J. Phys. Chem. 85: 1069 (1981).CrossRefGoogle Scholar
  45. 37.
    H. Fujihara, J.-J. Chiu, and N. Furukawa, J. Am. Chem. Soc. 110: 1280 (1988).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1990

Authors and Affiliations

  • Richard S. Glass
    • 1
  1. 1.Department of ChemistryThe University of ArizonaTucsonUSA

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