Pfitzner–Moffatt oxidation

The Pfitzner - Moffatt oxidation, often simply Moffat oxidation, is a mild oxidizing method, the primary and secondary alcohols, with N, N '- dicyclohexylcarbodiimide (DCC) and dimethyl sulfoxide (DMSO ) into the respective aldehyde or ketone. Special note here is that the oxidation of primary alcohols in stops after the first oxidation step and not extending to the carboxylic acid, as is the case with a conventional treatment with oxidizing agents.

Similar reactions are the Swern oxidation ( higher yield with fewer by-products ), the Dess- Martin oxidation, the Julia oxidation or oxidation with pyridinium chlorochromate.

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Reaction mechanism

In the first step, the dimethyl sulfoxide ( DMSO), N, N'- dicyclohexylcarbodiimide (DCC) is activated.

The activated DMSO is now attacked by the nucleophilic alcohol. By rearrangement and cleavage occurs as a reactive intermediate, a mesomeric stabilized Alkoxysulfonium ylide. Re rearrangements and elimination of dimethyl sulfide gives the final product.