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Posted by
Michael Romeo

m-CPBA Selectivity between Baeyer Villiger Oxidation and Epoxidation?

If both a ketone and an alkene are present in a molecule and you add one equivalent of m-CPBA, what are the factors that determine which group will be oxidized, the ketone through Baeyer-Villiger oxidation or the alkene through concerted epoxidation? Is one of the reactions particularly faster and better than the other?

EDIT: Since the literature seems to be conflicted and there is not a clear general answer, let us take the below as an example because I am interested in the competing factors here. For this example, I am leaning towards epoxidation just due to electron-rich alkene, and there is no base to make m-CPBA a better nucleophile for BV. enter image description here

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