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Part of the book series: Advanced Organic Chemistry ((AOCB))

Abstract

This chapter is concerned with reactions which transform a functional group to a more highly oxidized derivative. There is a very large number of such processes, and the reactions have been chosen for discussion on the basis of general utility in organic synthesis. As the reactions are considered, it will become evident that the material in this chapter spans a wider variety of mechanistic patterns than is true for most of the earlier chapters. Because of this range in mechanisms, the chapter has been organized by the functional-group transformation that is accomplished. This organization facilitates comparison of the methods available for effecting a given synthetic transformation. In general, oxidants have been grouped into three classes: transition metal drivatives; oxygen, ozone, and peroxides; and other reagents.

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General References

  1. R. L. Augustine (ed.), Oxidations, Vol. 1, Marcel Dekker, New York, 1969.

    Google Scholar 

  2. R. L. Augustine and D. J. Trecker (eds.), Oxidations, Vol. 2, Marcel Dekker, New York, 1971.

    Google Scholar 

  3. P. S. Bailey, Ozonization in Organic Synthesis, Vols. I and II, Academic Press, New York, 1978, 1982.

    Google Scholar 

  4. G. Cainelli and G. Cardillo, Chromium Oxidations in Organic Chemistry, Springer-Verlag, New York, 1984.

    Book  Google Scholar 

  5. L. J. Chinn, Selection of Oxidants in Synthesis, Marcel Dekker, New York, 1971.

    Google Scholar 

  6. A. A. Frimer, Chem. Rev. 79, 359 (1979).

    Article  CAS  Google Scholar 

  7. A. H. Haines, Methods for the Oxidation of Organic Compounds; Alkanes, Alkenes, Alkynes and Arynes, Academic Press, Orlando, Florida, 1985.

    Google Scholar 

  8. W. J. Mijs and C. R. H. de Jonge, Organic Synthesis by Oxidation with Metal Compounds, Plenum, New York, 1986.

    Book  Google Scholar 

  9. W. Trahanovsky (ed.), Oxidations in Organic Chemistry, Parts B-D, Academic Press, New York, 1973–1982.

    Google Scholar 

  10. H. H. Wasserman and R. W. Murray (eds.), Singlet Oxygen, Academic Press, New York, 1979.

    Google Scholar 

  11. K. B. Wiberg (ed.), Oxidations in Organic Chemistry, Part A, Academic Press, New York, 1965.

    Google Scholar 

  12. Y. Butsugan, S. Yoshida, M. Muto, and T. Bito, Tetrahedron Lett, 1129 (1971).

    Google Scholar 

  13. E. J. Corey and H. E. Ensley, J. Am. Chem. Soc. 97, 6908 (1975).

    Article  CAS  Google Scholar 

  14. R. G. Gaughan and C. D. Poulter, J. Org. Chem. 44, 2441 (1979).

    Article  CAS  Google Scholar 

  15. E. Vedejs, D. A. Engler, and J. E. Telschow, J. Org. Chem. 43, 188 (1978).

    Article  CAS  Google Scholar 

  16. K. Akashi, R. E. Palermo, and K. B. Sharpless, J. Org. Chem. 43, 2063 (1978).

    Article  CAS  Google Scholar 

  17. A. Hassner, R. H. Reuss, and H. W. Pinnick, J. Org. Chem. 40, 3427 (1975).

    Article  CAS  Google Scholar 

  18. R. N. Mirrington and K. J. Schmalzl, J. Org. Chem. 37, 2877 (1972).

    Article  CAS  Google Scholar 

  19. K. B. Sharpless and R. F. Lauer, J. Org. Chem. 39, 429 (1974).

    Article  CAS  Google Scholar 

  20. J. A. Marshall and R. C. Andrews, J. Org. Chem. 50, 1602 (1985).

    Article  CAS  Google Scholar 

  21. R. H. Schlessinger, J. J. Wood, A. J. Poos, R. A. Nugent, and W. H. Parsons, J. Org. Chem. 48, 1146 (1983).

    Article  CAS  Google Scholar 

  22. R. K. Boeckman, Jr., J. E. Starett, Jr., D. G. Nickell, and P.-E. Sum, J. Am. Chem. Soc. 108, 5549 (1986).

    Article  CAS  Google Scholar 

  23. E. J. Corey and Y. B. Xiang, Tetrahedron Lett. 29, 995 (1988).

    Article  CAS  Google Scholar 

  24. D. J. Plata and J. Kallmerten, J. Am. Chem. Soc. 110, 4041 (1988).

    Article  CAS  Google Scholar 

  25. B. E. Rossiter, T. Katsuki, and K. B. Sharpless, J. Am. Chem. Soc. 103, 464 (1981).

    Article  CAS  Google Scholar 

  26. J. Mulzer, A. Angermann, B. Schubert, and C. Seilz, J. Org. Chem. 51, 5294 (1986).

    Article  CAS  Google Scholar 

  27. R. H. Schlessinger and R. A. Nugent, J. Am. Chem. Soc. 104, 1116 (1982).

    Article  CAS  Google Scholar 

  28. H. Niwa, T. Mori, T. Hasegawa, and K. Yamada, J. Org. Chem. 51, 1015 (1986).

    Article  CAS  Google Scholar 

  29. J. P. McCormick, W. Tomasik, and M. W. Johnson, Tetrahedron Lett., 607 (1981).

    Google Scholar 

  30. H. C. Brown, J. H. Kawakami, and S. Ikegami, J. Am. Chem. Soc. 92, 6914 (1970).

    Article  CAS  Google Scholar 

  31. R. M. Scarborough, Jr., B. H. Toder, and A. B. Smith III, J. Am. Chem. Soc. 102, 3904 (1980).

    Article  CAS  Google Scholar 

  32. B. Rickborn and R. M. Gerkin, J. Am. Chem. Soc. 90, 4193 (1968).

    Article  CAS  Google Scholar 

  33. J. A. Marshall and R. A. Rüden, J. Org. Chem. 36, 594 (1971).

    Article  CAS  Google Scholar 

  34. G. A. Kraus and B. Roth, J. Org. Chem. 45, 4825 (1980).

    Article  CAS  Google Scholar 

  35. T. Sakan and K. Abe, Tetrahedron Lett., 2471 (1968).

    Google Scholar 

  36. K. J. Clark, G. I. Fray, R. H. Jaeger, and R. Robinson, Tetrahedron 6, 217 (1959).

    Article  CAS  Google Scholar 

  37. T. Kawabata, P. Grieco, H.-L. Sham, H. Kim, J. Y. Jaw, and S. Tu, J. Org. Chem. 52, 3346 (1987).

    Article  CAS  Google Scholar 

  38. P. T. Lansbury, J. P. Galbo, and J. P. Springer, Tetrahedron Lett. 29, 147 (1988).

    Article  CAS  Google Scholar 

  39. J. P. Marino, R. F. de la Pradilla, and E. Laborde, J. Org. Chem. 52, 4898 (1987).

    Article  CAS  Google Scholar 

  40. J. A. Marshall and R. A. Rüden, J. Org. Chem. 36, 594 (1971).

    Article  CAS  Google Scholar 

  41. J. E. Toth, P. R. Hamann, and P. L. Fuchs, J. Org. 53, 4694 (1988).

    Article  CAS  Google Scholar 

  42. E. L. Eliel, S. H. Schroeter, T. J. Brett, F. J. Biros, and J.-C. Richer, J. Am. Chem. Soc. 88, 3327 (1966).

    Article  CAS  Google Scholar 

  43. E. E. Royals and J. C. Leffingwell, J. Org. Chem. 31, 1927 (1966).

    Article  Google Scholar 

  44. W. W. Epstein and F. W. Sweat, Chem. Rev. 67, 247 (1967).

    Article  CAS  Google Scholar 

  45. D. P. Higley and R. W. Murray, J. Am. Chem. Soc. 96, 3330 (1974).

    Article  CAS  Google Scholar 

  46. R. Criegee and P. Günther, Chem. Ber. 96, 1564 (1963).

    Article  CAS  Google Scholar 

  47. S. Isoe, S. Katsumura, S. B. Hyeon, and T. Sakan, Tetrahedron Lett., 1089 (1971).

    Google Scholar 

  48. Y. Ogata, Y. Sawaki, and M. Shiroyama, J. Org. Chem. 42, 4061 (1977).

    Article  CAS  Google Scholar 

  49. F. G. Bordwell and A. C. Knipe, J. Am. Chem. Soc. 93, 3416 (1971).

    Article  CAS  Google Scholar 

  50. B. M. Trost, P. R. Bernstein, and P. C. Funfschilling, J. Am. Chem. Soc. 101, 4378 (1979).

    Article  CAS  Google Scholar 

  51. C. S. Foote, S. Mazur, P. A. Burns, and D. Lerdal, J. Am. Chem. Soc. 95, 586 (1973).

    Article  CAS  Google Scholar 

  52. J. P. Marino, K. E. Pfitzner, and R. A. Olofson, Tetrahedron 27, 4181 (1971).

    Article  CAS  Google Scholar 

  53. M. A. Avery, C. Jennings-White, and W. K. M. Chong, Tetrahedron Lett. 28, 4629 (1987).

    Article  CAS  Google Scholar 

  54. P. N. Confalone, C. Pizzolato, D. L. Confalone, and M. R. Uskokovic, J. Am. Chem. Soc. 102, 1954 (1980).

    Article  CAS  Google Scholar 

  55. S. Danishefsky, R. Zamboni, M. Kahn, and S. J. Etheredge, J. Am. Chem. Soc. 103, 3460 (1981).

    Article  CAS  Google Scholar 

  56. J. K. Whitesell, R. S. Matthews, M. A. Minton, and A. M. Helbling, J. Am. Chem. Soc. 103, 3468 (1981).

    Article  CAS  Google Scholar 

  57. F. A. J. Kerdesky, R. J. Ardecky, M. V. Lakshmikanthan, and M. P. Cava, J. Am. Chem. Soc. 103, 1992 (1981).

    Article  CAS  Google Scholar 

  58. J. K. Whitesell and R. S. Matthews, J. Org. Chem. 43, 1650 (1978).

    Article  CAS  Google Scholar 

  59. R. Fujimoto, Y. Kishi, and J. F. Blount, J. Am. Chem. Soc. 102, 7154 (1980).

    Article  CAS  Google Scholar 

  60. S. P. Tanis and K. Nakanishi, J. Am. Chem. Soc. 101, 4398 (1979).

    Article  CAS  Google Scholar 

  61. R. B. Miller and R. D. Nash, J. Org. Chem. 38, 4424 (1973).

    Article  CAS  Google Scholar 

  62. R. Grewe and I. Hinrichs, Chem. Ber. 97, 443 (1964).

    Article  CAS  Google Scholar 

  63. W. Nagata, S. Hirai, K. Kawata, and T. Okumura, J. Am. Chem. Soc. 89, 5046 (1967).

    Article  CAS  Google Scholar 

  64. W. G. Dauben, M. Lorber, and D. S. Fullerton, J. Org. Chem. 34, 3587 (1969).

    Article  CAS  Google Scholar 

  65. E. E. van Tamelen, M. Shamma, A. W. Burgstahler, J. Wolinsky, R. Tamm, and P. E. Aldrich, J. Am. Chem. Soc. 80, 5006 (1958).

    Article  Google Scholar 

  66. S. D. Burke, C. W. Murtishaw, J. O. Saunders, J. A. Oplinger, and M. S. Dike, J. Am. Chem. Soc. 106, 4558 (1984).

    Article  CAS  Google Scholar 

  67. B. M. Trost, P. G. McDougal, and K. J. Haller, J. Am. Chem. Soc. 106, 383 (1984).

    Article  CAS  Google Scholar 

  68. W. P. Keaveney, M. G. Berger, and J. J. Pappas, J. Org. Chem. 32, 1537 (1967).

    Article  CAS  Google Scholar 

  69. B. M. Trost and K. Hiroi, J. Am. Chem. Soc. 97, 6911 (1975).

    Article  CAS  Google Scholar 

  70. E. C. Taylor, C.-S. Chiang, A. McKillop, and J. F. White, J. Am. Chem. Soc. 98, 6750 (1976).

    Article  CAS  Google Scholar 

  71. F. Delay and G. Ohloff, Helv. Chim. Acta 62, 2168 (1979).

    Article  CAS  Google Scholar 

  72. R. Noyori, T. Sato, and Y. Hayakawa, J. Am. Chem. Soc. 100, 2561 (1978).

    Article  CAS  Google Scholar 

  73. I. Saito, R. Nagata, K. Yubo, and Y. Matsuura, Tetrahedron Lett. 24, 4439 (1983).

    Article  CAS  Google Scholar 

  74. J. R. Wiseman and S. Y. Lee, J. Org. Chem. 51, 2485 (1986).

    Article  CAS  Google Scholar 

  75. H. Nishiyama, M. Matsumoto, H. Arai, H. Sakaguchi, and K. Itoh, Tetrahedron Lett. 27, 1599 (1986).

    Article  CAS  Google Scholar 

  76. R. E. Ireland, P. G. M. Wuts, and B. Ernst, J. Am. Chem. Soc. 103, 3205 (1981).

    Article  CAS  Google Scholar 

  77. R. M. Scarborough, Jr., B. H. Toder, and A. B. Smith III, J. Am. Chem. Soc. 102, 3904 (1980).

    Article  CAS  Google Scholar 

  78. P. F. Hudrlik, A. M. Hudrlik, G. Nagendrappa, T. Yimenu, E. T. Zellers, and E. Chin, J. Am. Chem. Soc. 102, 6894 (1980).

    Article  CAS  Google Scholar 

  79. T. Wakamatsu, K. Akasaka, and Y. Ban, J. Org. Chem. 44, 2008 (1979).

    Article  CAS  Google Scholar 

  80. D. A. Evans, C. E. Sacks, R. A. Whitney, and N. G. Mandel, Tetrahedron Lett. 727 (1978).

    Google Scholar 

  81. F. Bourelle-Wargnier, M. Vincent, and J. Chuche, J. Org. Chem. 45, 428 (1980).

    Article  CAS  Google Scholar 

  82. J. A. Zalikowski, K. E. Gilbert, and W. T. Borden, J. Org. Chem. 45, 346 (1980).

    Article  CAS  Google Scholar 

  83. E. Vogel, W. Klug, and A. Breuer, Org. Synth. 55, 86 (1976).

    CAS  Google Scholar 

  84. L. D. Spicer, M. W. Bullock, M. Garber, W. Groth, J. J. Hand, D. W. Long, J. L. Sawyer, and R. S. Wayne, J. Org. Chem. 33, 1350 (1968).

    Article  CAS  Google Scholar 

  85. B. E. Rossiter, T. Katsuki, and K. B. Sharpless, J. Am. Chem. Soc. 103, 464 (1981).

    Article  CAS  Google Scholar 

  86. L. A. Paquette and Y.-K. Han, J. Am. Chem. Soc. 103, 1831 (1981).

    Article  CAS  Google Scholar 

  87. T. Wakamatsu, K. Akasaka, and Y. Ban, Tetrahedron Lett., 2755 (1977).

    Google Scholar 

  88. M. Muelbacher and C. D. Poulter, J. Org. Chem. 53, 1026 (1988).

    Article  Google Scholar 

  89. P. T. W. Cheng and S. McLean, Tetrahedron Lett. 29, 3511 (1988).

    Article  CAS  Google Scholar 

  90. A. B. Smith III and R. E. Richmond, J. Am. Chem. Soc. 105, 575 (1983).

    Article  CAS  Google Scholar 

  91. R. K. Boeckman, Jr., J. E. Starrett, Jr., D. G. Nickell, and P.-E. Sum, J. Am. Chem. Soc. 108, 15549 (1986).

    Article  Google Scholar 

  92. Y. Gao and K. B. Sharpless, J. Org. Chem. 53, 4081 (1988).

    Article  CAS  Google Scholar 

  93. C. W. Jefford, Y. Wang, and G. Bernardinelli, Helv. Chim. Acta 71, 2042 (1988).

    Article  CAS  Google Scholar 

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© 1990 Plenum Press, New York

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Carey, F.A., Sundberg, R.J. (1990). Oxidations. In: Advanced Organic Chemistry. Advanced Organic Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-9797-7_12

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  • DOI: https://doi.org/10.1007/978-1-4613-9797-7_12

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