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.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 51 print issues and online access
$199.00 per year
only $3.90 per issue
Buy this article
- Purchase on Springer Link
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
Similar content being viewed by others
References
Ball, S., Goodwin, T. W., and Morton, R. A., Biochem. J., 42, 516 (1948).
Evans, R. M., Quart. Rev., 13, 61 (1959).
Gritter, R. J., and Wallace, T. J., J. Org. Chem., 24, 1051 (1959).
Henbest, H. B., and Stratford, M. J. W., Chem. and Indust., 1170 (1961).
Pratt, E. F., and van de Castle, J. F., J. Org. Chem., 26, 2973 (1961).
Pratt, E. F., and Suskind, S. P., ibid., 28, 638 (1963).
Glemser, O., and Gattow, G., Naturwiss., 47, 59 (1960). Gattow, G., and Wendlandt, H. G., Z. Anal. Chem., 174, 15 (1960).
Rosenkranz, G., Sondheimer, F., and Mancera, O., J. Chem. Soc., 2189 (1953).
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).
Harfenist, M., Bavley, A., and Lazier, W. A., J. Org. Chem., 19, 1608 (1954).
Kolthoff, I. M., and Sandell, E. B., Textbook of Quantitative Inorganic Analysis, third ed., 116 (Macmillan Co., New York, 1952).
Uri, N., A.C.S. Adv. Chem. Series, No. 36, 102 (1962).
Burger, J., Meyer, C., Clement, J., and Balaceanu, J. C., C.R. Acad. Sci., Paris, 252, 2235 (1961).
George, P., Rideal, E. K., and Robertson, A., Proc. Roy. Soc., 185, 228 309 and 337 (1946).
Fordham, L. W. L., and Williams, H. L., Canad. J. Res., 283, 551 (1950).
Saier, E. L., and Hughes, R. H., Anal. Chem., 30, 513 (1958).
Bellamy, L. J., The Infra-red Spectra of Complex Molecules (John Wiley and Sons, Inc., New York, 1954).
Iddles, H. A., and Jackson, C. E., Indust. Eng. Chem. (Anal. Ed.), 6, 454 (1934).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
GRITTER, R., DUPRE, G. & WALLACE, T. Oxidation of Benzyl Alcohols with Manganese Dioxide. Nature 202, 179–181 (1964). https://doi.org/10.1038/202179a0
Issue Date:
DOI: https://doi.org/10.1038/202179a0
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.
