Abstract
Two recent reviews of peroxidation of organic compounds1,2 cite the fact that α,β-unsaturated ketones are oxidized by peracids to enol esters. A priori, however, one might expect one or more of three possible products and their hydrolysates. Thus, I and II would result from an attack of peracid at the carbonyl carbon followed by rearrangement according to the mechanism proposed by Criegee3, Friess4, and Doering5, while III Would be the consequence of an attack at the β-carbon of the conjugated system.
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References
Swern, Chem. Rev., 45, 1 (1949).
Criegee, Fortschr. Chem. Forsch., 1, 508 (1950).
Criegee, Ann., 560, 127 (1948).
Friess, J. Amer. Chem. Soc., 71, 2571 (1949).
Doering and Speers, J. Amer. Chem. Soc., 72, 5515 (1950).
Böeseken and Kremer, Rec. trav. chim., 50, 827 (1931).
Böeseken and Soesman, Rec. trav. chim., 52, 874 (1933).
Böeseken and Jacobs, Rec. trav. chim., 55, 786 (1936).
Julian, Meyer and Ryden, J. Amer. Chem. Soc., 72, 367 (1950).
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WENKERT, E., RUBIN, M. Peroxidation of Unsaturated Ketones. Nature 170, 708–709 (1952). https://doi.org/10.1038/170708b0
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DOI: https://doi.org/10.1038/170708b0
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