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Recent controversy on imidyl radical chemistry

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References

  1. C. Walling, Free Radical Chemistry, John Wiley & Sons, New York, N. Y., 1957, pp. 381–386.

    Google Scholar 

  2. L. Horner and E. H. Winkelmann, Angew. Chem., 71(1959)349.

    Article  CAS  Google Scholar 

  3. N.P. Bau-Hoi, Rec. Chem. Progr., 13(1952)30.

    Google Scholar 

  4. W.A. Thaller, Methods Free Radical Chem., 2(1969)721.

    Google Scholar 

  5. C. Djerassi, Chem. Rev., 43(1948)271.

    Article  CAS  Google Scholar 

  6. K. Ziegler, A. Spaeta, E. Schaaf, W. Schumann and E. Winkelmann, Liebigs. Ann., 551(1942)80.

    Article  CAS  Google Scholar 

  7. P.S. Skell and J.C. Day, Account Chem. Res., 11(1978)381.

    Article  CAS  Google Scholar 

  8. H. Schmid and P. Karrer, Helv. Chim. Acta, 29(1946)573.

    Article  CAS  Google Scholar 

  9. H.J. Dauben and L.L. McCoy, J. Am. Chem. Soc., 81(1959)4853; ibid., J. Am. Chem. Soc. J. Org. Chem., 24(1959)1577.

    Google Scholar 

  10. G.F. Bloomfield, J. Chem. Soc., (1944)114.

  11. R.E. Pearson and J.C. Martin, J. Am. Chem. Soc., 85(1963)354 3142

    Article  CAS  Google Scholar 

  12. J.H. Incremona and J.C. Martin, J. Am. Chem. Soc., 92(1970)627.

    Article  CAS  Google Scholar 

  13. G.A. Russel, C. DeBoer and K.M. Desmond, J. Am. Chem. Soc., 85(1963)365; G.A. Russel and K.M. Desmond, J. Am. Chem. Soc., 85(1963)3139.

    Article  Google Scholar 

  14. C. Walling, A.L. Rieger and D.D. Tanner, J. Am. Chem. Soc., 85(1963)3129; C. Walling and A.L. Rieger, J. Am. Chem. Soc., 85(1963)3134.

    Article  CAS  Google Scholar 

  15. P.S. Skell, D.L. Tuleen and P.D. Readio, J. Am. Chem. Soc., 85(1963)2849, 2850.

    Article  CAS  Google Scholar 

  16. J. Adam, P.A. Gosselain and P. Goldfinger, Nature, 171(1953)704; P.A. Gosselain, J. Adam and P. Goldfinger, Bull. Soc. Chim. Belg., 65(1956)533.

    Article  CAS  Google Scholar 

  17. K.B. Wiberg and L.H. Slaugh, J. Am. Chem. Soc., 80(1958)3033.

    Article  CAS  Google Scholar 

  18. F.L.J. Sixma and R.H. Riem, Koninkl. Ned. Akad. Wetenschap. Proc., 61B(1958)183.

    CAS  Google Scholar 

  19. B.P. McGrath and J.M. Tedder, Proc. Chem. Soc., (1961)80.

  20. E.C. Kooyman, R. van Helden and A.F. Bickel, Koninkl. Ned. Akad. Wetenschap. Proc., B56(1953)75.

    Google Scholar 

  21. K.J. Shea, D.C. Lewis and P.S. Skell, J. Am. Chem. Soc., 95(1973)7768; P.S. Skell and K.J. Shen, J. Am. Chem. Soc., 94(1972)6550.

    Article  CAS  Google Scholar 

  22. A.G. Davis, B.P. Roberts and J.M. Smith, J. Chem. Soc., Perkin II, (1972)2221.

    Google Scholar 

  23. G.R. Chalfont and J.M. Perkin, J. Chem. Soc., B(1970)401.

  24. C. Lagerkrantz and E. Forshult, Acta Chem. Scand., 23(1969)708.

    Article  Google Scholar 

  25. O.E. Edward, D.H. Paskovich and A.H. Redoch, Can. J. Chem., 51(1973)978.

    Article  Google Scholar 

  26. H.W. Johnson, Jr. and D.E. Bublitz, J. Am. Chem. Soc., 79(1957)753;ibid., J. Am. Chem. Soc. 80(1958)3150.

    Article  CAS  Google Scholar 

  27. J.C. Martin and P.D. Bartlett, J. Am. Chem. Soc., 79(1957)2533.

    Article  CAS  Google Scholar 

  28. L.H. Zalkow and C.D. Kennedy, J. Org. Chem., 29(1964)1240.

    Google Scholar 

  29. W.J. Bailey and J. Bello, J. Org. Chem., 20(1955)525.

    Article  CAS  Google Scholar 

  30. K. Sakai, N. Koga and J.-P. Anselme, Tetrahedron Lett., (1979)4543.

  31. J.M. Landesber and M. Siegel, J. Org. Chem., 35(1970)1074.

    Google Scholar 

  32. A. Guillemonat, G. Peiffer, J.C. Traynard and A. Leger, Bull. Soc. Chim. France, (1964)1192.

  33. J.R. Shelton and C. Cialdella, J. Org. Chem., 23(1958)1128.

    Article  CAS  Google Scholar 

  34. E.R. Buchman and D.R. Howton, J. Am. Chem. Soc., 70(1948)2517.

    Article  CAS  Google Scholar 

  35. W.A. Thaler, J. Am. Chem. Soc., 85(1963)2607.

    Article  CAS  Google Scholar 

  36. J.G. Traynham, E.E. Green, Y.S. Lee, F. Schweinsberg and C.E. Low, J. Am. Chem. Soc., 94(1972)6552; J.G. Traynham and Y.S. Lee, J. Am. Chem. Soc., 96(1974)3590.

    Article  CAS  Google Scholar 

  37. D.D. Tanner, D. Darwish, M.W. Mosher and N.J. Bunce, J. Am. Chem Soc., 91(1969) 7398.

    Article  CAS  Google Scholar 

  38. D.D. Tanner, J.E. Rowe, T. Pace and Y. Kosugi, J. Am. Chem. Soc., 95(1973)4705 and references therein.

    Article  CAS  Google Scholar 

  39. J.C. Day, L.J. Lindstrom and P.S. Skell, J. Am. Chem. Soc., 95(1974)5616.

    Article  Google Scholar 

  40. F.L. Lu, Y.M.A. Naguib, H. Kitadani and Y.L. Chow, Can. J. Chem., 591(1979)1967 and unpublished results.

    Article  Google Scholar 

  41. V. Calo, L. Lopez and G. Pesce, J. Chem. Soc., Perkin I, (1977)501.

    Article  Google Scholar 

  42. D.R. Houton, J. Am. Chem. Soc., 69(1947)2060; E.R. Buchanan and D.R. Houton, J. Am. Chem. Soc., 70(1948)2517.

    Article  Google Scholar 

  43. R.C. Petterson and A. Wambsgans, J. Am. Chem. Soc., 86(1964)1648.

    Article  CAS  Google Scholar 

  44. T.R. Beebe and F.M. Howard, J. Am. Chem. Soc., 91(1969)3379.

    Article  CAS  Google Scholar 

  45. E. Hedaya, R.L. Hinman, V. Schomaker, S. Theodoropulos and L.M. Kyle, J. Am. Chem. Soc., 89(1967)4875.

    Article  CAS  Google Scholar 

  46. T. Koenig and W. Brewer, J. Am. Chem. Soc., 86(1964)2728.

    Article  CAS  Google Scholar 

  47. F.R. Stermitz and D.W. Neiswander, J. Am. Chem. Soc., 95(1973)2630.

    Article  CAS  Google Scholar 

  48. M.J.S. Dewar, A.H. Pakiari and A.B. Pierini, J. Am. Chem. Soc., 104(1982)3234.

    Google Scholar 

  49. J. Lesserd, D. Griller and K.U. Ingold, J. Am. Chem. Soc., 102(1980)3262; W.C. Dannen and R.W. Gellert, J. Am. Chem. Soc., 102(1980)3264.

    Article  Google Scholar 

  50. T. Koenig and R.A. Wielsek, Tetrahedron Lett., (1975)2007.

  51. Y. Apeloig and R. Schreiber, J. Am. Chem. Soc., 102(1980)6146.

    Article  Google Scholar 

  52. T. Clark, J. Am. Chem. Soc., 101(1979)7746.

    Article  CAS  Google Scholar 

  53. A. Lund, P.O. Samskog, L. Eberson and S. Lunell, J. Phys. Chem., 86(1982)2458.

    Article  CAS  Google Scholar 

  54. J.C. Day, M.G. Katsaros, W.D. Kocher, A.E. Scott and P.S. Skell, J. Am. Chem. Soc., 101(1978)1950.

    Article  Google Scholar 

  55. P.S. Skell and J.C. Day, J. Am. Chem. Soc., 101(1978)1951.

    Article  Google Scholar 

  56. R.L. Tlumuk and P.S. Skell, J. Am. Chem. Soc., 104(1982)7267.

    Article  Google Scholar 

  57. R.L. Tlumuk, J.C. Day, J.P. Slanga and P.S. Skell, J. Am. Chem. Soc., 104(1982)7257.

    Article  Google Scholar 

  58. P.S. Skell, R.L. Tlumuk and S. Seshadri, J. Am. Chem. Soc., 105(1983)5125; private communication from Prof. P.S. Skell.

    Article  CAS  Google Scholar 

  59. K. Ody, A. Nechvatal and J.M. Tedder, J. Chem. Soc., Perkin II, (1976)521.

    Google Scholar 

  60. Y.L. Chow and M. Kitadani, unpublished results.

  61. R.W. Yip, Y.L. chow and C. Beddard, J. Chem. Soc. Chem. Comm., (1981)955 and unpublished results.

  62. Y.L. Chow and M.H. Kang, unpublished results.

  63. C. Walling, G.M. El-Taliawi and C.X. Zhao, J. Am. Chem. Soc., 105(1983)5119.

    Article  CAS  Google Scholar 

  64. D.D. Tanner, T.C.-S. Ruo, H. Takiguchi, A. Guillaume, D.W. Reed, B.P. Setiloane, S.L. Tan and C.P. Meintzner, J. Org. Chem., 48(1983)2743.

    Article  CAS  Google Scholar 

  65. A.J. Sessna, S.E. Sugamori, R.W. Yip, M.P. Lau, R.S. Snyder and Y.L. Chow, J. Am. Chem. Soc., 99(1977)4044.

    Article  Google Scholar 

  66. R.W. Yip, T. Vidoczy, R.W. Snyder and Y.L. Chow, J. Phys. Chem., 82(1978)1194.

    Article  CAS  Google Scholar 

  67. V. Malatesta and K.U. Ingold, J. Am. Chem. Soc., 95(1973)6400.

    Article  CAS  Google Scholar 

  68. J.N.S. Tam, R.W. Yip and Y.L. Chow, J. Am. Chem. Soc., 96(1974)4543.

    Article  CAS  Google Scholar 

  69. R. Sutcliffe, M. Anpo, A. Stolow and K.U. Ingold, J. Am. Chem. Soc., 104(1982)6064.

    Article  CAS  Google Scholar 

  70. J.A. Howard, Advan. Free Rad. Chem., 4(1970)49.

    Google Scholar 

  71. C. Walling and M.J. Givian, J. Am. Chem. Soc., 87(1965)3361.

    Article  CAS  Google Scholar 

  72. Y.L. Chow, Y.M.A. Naguib, J. Am. Chem. Soc., in press.

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  1. Department of Chemistry, Simon Fraser University, V5A 1S6, Burnaby, B.C., Canada

    Yuan L. Chow & Y. M. A. Naguib

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Chow, Y.L., Naguib, Y.M.A. Recent controversy on imidyl radical chemistry. Reviews of Chemical Intermediates 5, 325–345 (1984). https://doi.org/10.1007/BF03155672

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