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Oxidation of Benzyl Alcohols with Manganese Dioxide

Abstract

SINCE the time that Ball, Goodwin and Morton1 first used manganese dioxide to oxidize vitamin A to retinene, many investigators have used this reaction. Evans2 has summarized much of the uses and Gritter and Wallace3 have carried out an extensive investigation with regard to the efficiency of numerous manganese dioxides on the yields of the oxidations. Mechanistic considerations were present from the very beginning since Ball, Goodwin and Morton1 suggested that the oxidation occurred on the surface of the dioxide, Henbest4 suggested that the reaction was occurring by free radical intermediates on the surface of the dioxide and Pratt and van de Castle5 found that these intermediates would explain their results obtained with substituted benzyl alcohols. The latter authors proposed a mechanism consistent with the results available and it was one which could apply to compounds other than unsaturated alcohols6. The present study was concerned with rate changes with solvent, temperature, type of manganese dioxide and the conclusion which the evidence would permit about what is occurring on the surface of the dioxide in the oxidation.

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References

  1. 1

    Ball, S., Goodwin, T. W., and Morton, R. A., Biochem. J., 42, 516 (1948).

    CAS  Article  Google Scholar 

  2. 2

    Evans, R. M., Quart. Rev., 13, 61 (1959).

    CAS  Article  Google Scholar 

  3. 3

    Gritter, R. J., and Wallace, T. J., J. Org. Chem., 24, 1051 (1959).

    CAS  Article  Google Scholar 

  4. 4

    Henbest, H. B., and Stratford, M. J. W., Chem. and Indust., 1170 (1961).

  5. 5

    Pratt, E. F., and van de Castle, J. F., J. Org. Chem., 26, 2973 (1961).

    CAS  Article  Google Scholar 

  6. 6

    Pratt, E. F., and Suskind, S. P., ibid., 28, 638 (1963).

  7. 7

    Glemser, O., and Gattow, G., Naturwiss., 47, 59 (1960). Gattow, G., and Wendlandt, H. G., Z. Anal. Chem., 174, 15 (1960).

    ADS  Google Scholar 

  8. 8

    Rosenkranz, G., Sondheimer, F., and Mancera, O., J. Chem. Soc., 2189 (1953).

  9. 9

    Attenburrow, J., Cameron, A. F. B., Chapman, J. H., Evans, R. M., Hems, B. A., Jansen, A. B. A., and Walker, T., ibid., 1094 (1952).

  10. 10

    Harfenist, M., Bavley, A., and Lazier, W. A., J. Org. Chem., 19, 1608 (1954).

    CAS  Article  Google Scholar 

  11. 11

    Kolthoff, I. M., and Sandell, E. B., Textbook of Quantitative Inorganic Analysis, third ed., 116 (Macmillan Co., New York, 1952).

    Google Scholar 

  12. 12

    Uri, N., A.C.S. Adv. Chem. Series, No. 36, 102 (1962).

  13. 13

    Burger, J., Meyer, C., Clement, J., and Balaceanu, J. C., C.R. Acad. Sci., Paris, 252, 2235 (1961).

    CAS  Google Scholar 

  14. 14

    George, P., Rideal, E. K., and Robertson, A., Proc. Roy. Soc., 185, 228 309 and 337 (1946).

    Google Scholar 

  15. 15

    Fordham, L. W. L., and Williams, H. L., Canad. J. Res., 283, 551 (1950).

    Article  Google Scholar 

  16. 16

    Saier, E. L., and Hughes, R. H., Anal. Chem., 30, 513 (1958).

    CAS  Article  Google Scholar 

  17. 17

    Bellamy, L. J., The Infra-red Spectra of Complex Molecules (John Wiley and Sons, Inc., New York, 1954).

    Google Scholar 

  18. 18

    Iddles, H. A., and Jackson, C. E., Indust. Eng. Chem. (Anal. Ed.), 6, 454 (1934).

    CAS  Article  Google Scholar 

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GRITTER, R., DUPRE, G. & WALLACE, T. Oxidation of Benzyl Alcohols with Manganese Dioxide. Nature 202, 179–181 (1964). https://doi.org/10.1038/202179a0

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