Chemistry Forums for Students > Organic Chemistry Forum
Oxidation
Justinn343:
@rolnor I will be keeping my options limited to Acetic Acid for now (due to green chemistry purposes) however i was wondering if Acetic Acid can be combined with Ascorbic Acid (vitamin c) to reduce over oxidation when using Oxone as the main oxidising agent?
rolnor:
Ascorbic acid is in a enol-form so it containes a double-bond, this can react with oxone. It depends on how fast your wanted reaction is if this reaction competes. I also think oxone is not very "green", it can react with ketones and form dioxiranes, these can react with alkenes to form epoxides wich are alkylating. Oxone is a powerful disinfectant and therefore also cytotoxic.
https://en.wikipedia.org/wiki/Potassium_peroxymonosulfate
Justinn343:
@rolnor You're right but not long ago i was reading about an oxygenation reaction using green chemistry having oxone as the main oxidant, if I'm not mistaken.
It may not be "very green" but its better than thousands of other oxidants when comes to indole oxygenation in my opinion.
I was thinking of a 45min reaction using AcOH as a medium, Ascorbic Acid as a radical quencher and Oxone as the main oxidant.
Let me know what you think
rolnor:
I would first try without ascorbic acid, if it works, try with. Yes, I agree, chrome and manganese etc. are worse then oxone. I dont know if the oxidation with oxone is possible in slight acidic medium, I have no experience in this reaction.
Justinn343:
Yes, not a good idea when it comes to Aldehydes but should be fine with non aldehyed indoles in acidic or basic conditions.
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