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I was observing the following reaction:

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The only part I am confused on is the first step... why does the peroxide oxidize the reactant by attacking the alpha carbon of the carbonyl ester instead of oxidizing the carbonyl carbon directly? Is this because of steric hindrance?

On another guess, I see that the ester is an electron donating group in that the oxygen donates some density to the benzene, so the benzene associated with it is deactivated, where as the alpha carbon group is activated.

Does reaction at the alpha carbon, then, a result of an activated group being able to donate more electron density to the then formed hydroperoxide causing this attack to be more favored than compared to a carbonyl attack?

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  • $\begingroup$ Attack at carbonyl wouldn't oxidise anything. $\endgroup$
    – Mithoron
    Jun 10 at 13:39
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    $\begingroup$ Welcome to ChemSE. I researched this reaction on Chem. Absts. No luck. Could you cite the source of the reaction? Hydrogen peroxide itself is not a very good nucleophile while its anion is. If base is present at the outset, I can imagine the peroxide anion attacking the carbonyl first with loss of phenoxide and then intramolecular addition of the peracid anion to form peroxylactone 3 as an alternative mechanism. What are the precise conditions for the formation assuming it is formed at all? $\endgroup$
    – user55119
    Jun 10 at 14:40
  • $\begingroup$ The product looks like acridone but would be missing a hydrogen on the nitrogen. The nitrogen bonding looks weird in most of the structures shown in the mechanism. $\endgroup$ Jun 10 at 18:16
  • $\begingroup$ @Karsten Theis: Missed the lack of H on N. Too busy with the other side of the molecule. I am suspect of its authenticity. $\endgroup$
    – user55119
    Jun 10 at 18:25
  • $\begingroup$ Hey all. Ive seen this mechanism at other places using CL, but please see figure and cited reference: researchgate.net/figure/…. Someone said that an attack at carbonyl wouldn't oxidize anything? Can anyone confirm/expand on that? Aren't ketones able to be oxidized? $\endgroup$
    – John Doe
    Jun 10 at 22:14

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