Oxidations

  • Francis A. Carey
  • Richard J. Sundberg
Part of the Advanced Organic Chemistry book series

Abstract

This chapter will be concerned with reactions which transform a functional group to a more highly oxidized derivative. There are a very large number of such processes and the reactions have been chosen for discussion on the basis of their general utility in organic synthesis. As the mechanisms of the reactions are considered, it will become evident that the material in this chapter scans a wider variety of mechanistic patterns than is true for most of the earlier chapters. Because of this variety in mechanistic patterns, the chapter has been organized along the lines of the functional-group transformation that is accomplished. This organization f acilitates comparison of the methods available for effecting a given synthetic transformation, but has the less desirable result of scattering the reactions of a given oxidant, such as the permanganate ion, into several sections. In general, oxidants have been grouped into three classes: transition metal derivatives; oxygen, ozone and peroxides, and other oxidizing agents.

Keywords

Carbonyl Compound Ring Opening Transition Metal Oxidant Oxidative Cleavage Allylic Alcohol 
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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General References

  1. K. B. Wiberg (ed.), Oxidation in Organic Chemistry, Part A, Academic Press, New York (1965).Google Scholar
  2. W. S. Trahanovsky (ed.), Oxidation in Organic Chemistry, Part B, Academic Press, New York (1973).Google Scholar
  3. W. S. Trahanovsky (ed.), Oxidation in Organic Chemistry, Part C, Academic Press, New York (1978).Google Scholar
  4. R. L. Augustine (ed.), Oxidation, Vol. 1, Marcel Dekker, New York (1969).Google Scholar
  5. R. L. Augustine and D. J. Trecker (eds.), Oxidation, Vol. 2, Marcel Dekker, New York (1971).Google Scholar
  6. L. J. Chinn, Selection of Oxidants in Synthesis, Marcel Dekker, New York (1971).Google Scholar
  7. P. S. Bailey, Ozonation in Organic Chemistry, Vol. I, Academic Press, New York (1978)Google Scholar
  8. Vol. II, Academic Press, New York (1982).Google Scholar
  9. H. H. Wasserman and R. W. Murray, ed., Singlet Oxygen, Academic Press, New York (1979).Google Scholar
  10. 1a.
    Y. Butsugan, S. Yoshida, M. Muto, and T. Bito, Tetrahedron Lett. 1129 (1971).Google Scholar
  11. b. E. J. Corey and H. E. Ensley, J. Am. Chem. Soc. 97, 6908 (1975).CrossRefGoogle Scholar
  12. c. R. G. Gaughan and C. D. Poulter, Error! Hyperlink reference not valid Chem. 44, 2441 (1979).Google Scholar
  13. d. E. Vedejs, D. A. Engler, and J. E. Telschow, Error! Hyperlink reference not valid Chem. 43, 188 (1978).Google Scholar
  14. e. K. Akashi, R. E. Palermo, and K. B. Sharpless, Error! Hyperlink reference not valid Chem. 43, 2063 (1978).Google Scholar
  15. f. A. Hassner, R. H. Reuss, and H. W. Pinnick, Error! Hyperlink reference not valid Chem. 40, 3427 (1975).Google Scholar
  16. g. R. N. Mirrington and K. J. Schmalzl, Error! Hyperlink reference not valid Chem. 37, 2877 (1972).Google Scholar
  17. h. K. B. Sharpless and R. F. Lauer, J Org. Chem. 39, 429 (1974).CrossRefGoogle Scholar
  18. 2.
    E. L. Eliel, S. H. Schroeter, T. J. Brett, F. J. Biros, and J.-C. Richer, J. Am. Chem. Soc. 88, 3327 (1966).CrossRefGoogle Scholar
  19. 3a.
    J. P. McCormick, W. Tomasik, and M. W. Johnson, Tetrahedron Lett. 607 (1981).Google Scholar
  20. b. H. C. Brown, J. H. Kawakami, and S. Ikegami, J. Am. Chem. Soc. 92, 6914 (1970).CrossRefGoogle Scholar
  21. c. R. M. Scarborough, Jr., B. H. Toder, and A. B. Smith, III, J. Am. Chem. Soc. 102, 3904 (1980).CrossRefGoogle Scholar
  22. d. B. Rickborn and R. M. Gerkin, J. Am. Chem. Soc. 90, 4193 (1968).CrossRefGoogle Scholar
  23. e. J. A. Marshall and R. A. Ruden, Error! Hyperlink reference not valid Chem. 36, 594 (1971).Google Scholar
  24. f. G. A. Kraus and B. Roth, Error! Hyperlink reference not valid Chem. 45, 4825 (1980).Google Scholar
  25. g. T. Sakan and K. Abe, Tetrahedron Lett. 2471 (1968).Google Scholar
  26. h. K. J. Clark, G. I. Fray, R. H. Jaeger, and R. Robinson, Tetrahedron 6, 217 (1959).Google Scholar
  27. 4.
    E. E. Royals and J. C. Leffingwell, Error! Hyperlink reference not valid Chem. 31, 1937 (1966).Google Scholar
  28. 5.
    W. W. Epstein and F. W. Sweat, Chem. Rev. 67, 247 (1967).CrossRefGoogle Scholar
  29. 6.
    D. P. Higley and R. W. Murray, J. Am. Chem. Soc. 96, 3330 (1974).CrossRefGoogle Scholar
  30. 7.
    R. Criegee and P. Günther, Chem. Ber. 96, 1564 (1963).CrossRefGoogle Scholar
  31. 8.
    W. P. Keaveney, M. G. Berger, and J. J. Pappas, Error! Hyperlink reference not valid Chem. 32, 1537 (1967).Google Scholar
  32. 9a.
    S. Isoe, S. Katsumura, S. B. Hyeon, and T. Sakan, Tetrahedron Lett. 1089 (1971).Google Scholar
  33. b. Y. Ogata, Y. Sawaki, and M. Shiroyama, Error! Hyperlink reference not valid Chem. 42, 4061 (1977).Google Scholar
  34. c. F. G. Bordwell and A. C. Knipe, J. Am. Chem. Soc. 93, 3416 (1971).CrossRefGoogle Scholar
  35. d. B. M. Trost, P. R. Bernstein, and P. C. Funfschilling, J. Am. Chem. Soc. 101, 4378 (1979).CrossRefGoogle Scholar
  36. e. C. S. Foote, S. Mazur, P. A. Burns, and D. Lerdal, J. Am. Chem. Soc. 95, 586 (1973).CrossRefGoogle Scholar
  37. f. J. P. Marino, K. E. Pfitzner, and R. A. Olofson, Tetrahedron 27, 4181 (1971).CrossRefGoogle Scholar
  38. 10a.
    P. N. Confalone, C. Pizzolato, D. L. Confalone, and M. R. Uskokovic, J. Am. Chem. Soc. 102, 1954 (1980).CrossRefGoogle Scholar
  39. b. S. Danishefsky, R. Zamboni, M. Kahn, and S. J. Etheredge, J. Am. Chem. Soc. 103, 3460 (1981).CrossRefGoogle Scholar
  40. c. J. K. Whitesell, R. S. Matthews, M. A. Minton, and A. M. Helbling, J. Am. Chem. Soc. 103, 3468 (1981).CrossRefGoogle Scholar
  41. d. F. A. J. Kerdesky, R. J. Ardecky, M. V. Lakshmikanthan, and M. P. Cava, J. Am. Chem. Soc. 103, 1992 (1981).CrossRefGoogle Scholar
  42. e. J. K. Whitesell and R. S. Matthews, Error! Hyperlink reference not valid Chem. 43, 1650 (1978).Google Scholar
  43. f. R. Fujimoto, Y. Kishi, and J. F. Blount, J. Am. Chem. Soc. 102, 7154 (1980).CrossRefGoogle Scholar
  44. g. S. P. Tanis and K. Nakanishi, J. Am. Chem. Soc. 101, 4398 (1979).CrossRefGoogle Scholar
  45. h. R. B. Miller and R. D. Nash, Error! Hyperlink reference not valid Chem. 38, 4424 (1973).Google Scholar
  46. i. R. Grewe and I. Hinrichs, Chem. Ber. 97, 443 (1964).CrossRefGoogle Scholar
  47. j. W. Nagata, S. Hirai, K. Kawata, and T. Okumura, J. Am. Chem. Soc. 89, 5046 (1967).CrossRefGoogle Scholar
  48. k. W. G. Dauben, M. Lorber, and D. S. Fullerton, Error! Hyperlink reference not valid Chem. 34, 3587 (1969).Google Scholar
  49. l. E. E. van Tamelen, M. Shamma, A. W. Burgstahler, J. Wolinsky, R. Tamm, and P. E. Aldrich, J. Am. Chem. Soc. 80, 5006 (1958).CrossRefGoogle Scholar
  50. 11a.
    F. Delay and G. Ohloff, Heln. Chim. Acta 62, 2168 (1979).CrossRefGoogle Scholar
  51. b. R. Noyori, T. Sato, and Y. Hayakawa, J. Am. Chem. Soc. 100, 2561 (1978).CrossRefGoogle Scholar
  52. 12a.
    R. E. Ireland, P. G. M. Wuts, and B. Ernst, J. Am. Chem. Soc. 103, 3205 (1981).CrossRefGoogle Scholar
  53. b. R. M. Scarborough, Jr., B. H. Toder, and A. B. Smith, III, J. Am. Chem. Soc. 102, 3904 (1980).CrossRefGoogle Scholar
  54. c. P. F. Hudrlik, A. M. Hudrlik, G. Nagendrappa, T. Yimenu, E. T. Zellers, and E. Chin, J. Am. Chem. Soc. 102, 6894 (1980).CrossRefGoogle Scholar
  55. d. T. Wakamatsu, K. Akasaka, and Y. Ban, Error! Hyperlink reference not valid Chem. 44, 2008 (1979).Google Scholar
  56. e. D. A. Evans, C. E. Sacks, R. A. Whitney, and N. G. Mandel, Tetrahedron Lett. 727 (1978).Google Scholar
  57. f. F. Bourelle-Wargnier, M. Vincent, and J. Chuche, Error! Hyperlink reference not valid Chem. 45, 428 (1980).Google Scholar
  58. g. J. A. Zalikowski, K. E. Gilbert, and W. T. Borden, Error! Hyperlink reference not valid Chem. 45, 346 (1980).Google Scholar
  59. h. E. Vogel, W. Klug, and A. Breuer, Org. Synth. 55, 86 (1976).Google Scholar
  60. i. L. D. Spicer, M. W. Bullock, M. Garber, W. Groth, J. J. Hand, D. W. Long, J. L. Sawyer, and R. S. Wayne, Error! Hyperlink reference not valid Chem. 33, 1350 (1968).Google Scholar
  61. j. B. E. Rossiter, T. Katsuki, and K. B. Sharpless, J. Am. Chem. Soc. 103, 464 (1981).CrossRefGoogle Scholar
  62. 13.
    B. M. Trost and K. Hiroi, J. Am. Chem. Soc. 97, 6911 (1975).CrossRefGoogle Scholar
  63. 14.
    E. C. Taylor, C.-S. Chiang, A. McKillop, and J. F. White, J. Am. Chem. Soc. 98, 6750 (1976).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1983

Authors and Affiliations

  • Francis A. Carey
    • 1
  • Richard J. Sundberg
    • 1
  1. 1.University of VirginiaCharlottesvilleUSA

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