Abstract
The two monoepoxides resulting from the epoxidation of methyl linoleate with monoperphthalic acid have been separated from each other by column chromatography. Degradation reactions on each of these established that the separation occurred without concomitant rearrangement of the double bond or the epoxide ring. Thus, (±)-methyl vernolate (I) and (±)-methyl coronarate (II) were obtained in a pure state.
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Maerker, G., E. T. Haeberer and W. C. Ault, JAOCS43, 100–104 (1966).
Canonica, L., M. Ferrari, U. M. Pagnoni, F. Pelizzoni, S. Maromi and T. Salvatori, in press.
Smith, C. R., M. O. Bagby, R. L. Lohnar, C. A. Glass and I. A. Wolff, J. Org. Chem.25 218–222 (1960).
Payne, G. B., Org. Synth.42, 77–78 (1962).
McKay, A. F., and A. R. Bader, J. Org. Chem.13, 75–85 (1948).
Osbond, J. M., J. Chem. Soc. 5270–5275 (1961).
Morris, L. J., Chem. Ind. 1238–1240 (1962).
Nakanishi, K., Infrared Absorption Spectroscopy, Holden-Day, Inc., San Francisco, 1962, p. 24.
Schreve, O. D., M. R. Heether, H. B. Knight and Daniel Swern, Anal. Chem.23, 277–285 (1951); Patterson, W. A., Ibid.26, 823–835 (1954).
Gunstone, F. D., J. Chem. Soc. 1611–1616 (1954).
Jones, E. P., and J. A. Stolp, JAOCS35, 71–76 (1958).
Hopkins, C. Y., and H. J. Bernstein, Can. J. Chem.37, 775–782 (1959).
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Ferrari, M., Ghisalberti, E.L., Pagnoni, U.M. et al. Monoepoxidation of methyl linoleate: (±)-methyl vernolate and (±)-methyl coronarate. J Am Oil Chem Soc 45, 649–651 (1968). https://doi.org/10.1007/BF02541248
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DOI: https://doi.org/10.1007/BF02541248