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Oxidation

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Justinn343:
Recently I have been wondering why Acetone is obligatory to use as solvent in oxidation with other oxidising agents, i know it is a mild oxidiser and neutralises hydroxy radicals but could there be another alternative to it in the fields of green chemistry? Maybe Ascorbic Acid in H2O?

rolnor:
acetone was used from long time ago with Jones reagent, I think you can use other solvents as well. Ascorbic acid reacts fast with KMnO4 so its probably not so good.

Justinn343:
Which other solvents can be used?
Also is it necessary to use those solvents in combination with the main oxidizer?

Justinn343:
If Acetone is an oxidant why is it used to reduce over oxidation  ??? ??? And Why is it perferred for indoles to be oxidised in basic conditions and not acidic?

Looking forwards to your replies,

Justin

rolnor:
It depends on the oxidation reagent. Jones reagent is aqueous so maybe dioxane, DMF (not DMSO), maybe THF, acetonitrile.
KMnO4 is also water-soluble so its similar. I think there is tetrabutylamoniumpermanganate also so this could be used in DCM, EtOAc etc. Acetic acid would also be fine in all cases.  I have no reference to these suggestions, its just my thoughts.
No, you can use just water but often your startingmaterial is not soluble in just water, you need a co-solvent.

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