I am attempting to cleave a double bond into a carboxylic acid and carbon dioxide using an ozonolysis reaction followed by an oxidative workup. I am concerned with the presence of a tertiary ether in my reactant, however. I am planning on using standard ozonolysis procedures as described in Vogel's Textbook of Practical Organic Chemistry on page 592 using an oxidative workup with either potassium permanganate or hydrogen peroxide. I am worried that the oxidative conditions will also affect the tertiary ether. I cannot find any literature detailing the compatibility of tertiary ethers with peroxide or permanganate. Is there another protocol that would be milder on my substrate, or does it seem as though this reaction would not affect other functional groups? Here is my scheme:

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  • 2
    $\begingroup$ I don't think this will be a problem. Tertiary ethers are pretty robust. $\endgroup$
    – Waylander
    Commented Nov 30, 2019 at 8:27
  • 2
    $\begingroup$ Oxidation of ethers is normally an issue of there is a C-H bond directly adjacent to the oxygen. Your molecule has neither. $\endgroup$
    – Beerhunter
    Commented Nov 30, 2019 at 11:06
  • $\begingroup$ Since oxidation is not an issue, would using the permanganate workup be more effective due to the possibility of the formation of tertiary and benzyl radicals using the peroxide? $\endgroup$
    – Eli Jones
    Commented Nov 30, 2019 at 14:36
  • $\begingroup$ But you can't form any tertiary or benzyl radicals. There are no tertiary C-H or benzylic H's to abstract. $\endgroup$ Commented Nov 30, 2019 at 23:50
  • $\begingroup$ As an alternative, consider RuO4/NaIO4. en.wikipedia.org/wiki/Ruthenium_tetroxide $\endgroup$
    – user55119
    Commented Dec 1, 2019 at 1:08


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