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When the above compound is subjected to acidified $\ce{KMnO4}$, can both side chain oxidation and oxidative cleavage of $\ce{C=C}$ bond occur? Or will one have priority over the other?

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  • $\begingroup$ It will depend on the reaction conditions used. I think it would be possible to find conditions that give majority oxidative cleavage. $\endgroup$
    – Waylander
    Commented Sep 8, 2021 at 6:32
  • $\begingroup$ @Waylander what kind of conditions would favor oxidative cleavage over side-chain oxidation? I thought the reactants and conditions are largely similar for the two? $\endgroup$
    – john
    Commented Sep 8, 2021 at 9:04
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    $\begingroup$ Lower concentrations and reaction temperature. But if you want selective oxidative cleavage there are better reagents to use. $\endgroup$
    – Waylander
    Commented Sep 8, 2021 at 9:38

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