Organic Synthesis
NamedReactions
Mechanism: Pfitzner Moffatt Oxidation
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From Wikipedia, the free encyclopedia Stoichiometry and mechanism
In terms of mechanism, the reaction is proposed to involve the intermediary of an sulfonium group, formed by a reaction between DMSO and the carbodiimide. This species is highly reactive and is attacked by the alcohol. Rearrangement give an alkoxysulfonium ylide which decomposes to give dimethyl sulfide and the carbonyl compound. This reaction has been largely displaced by the Swern oxidation, which also uses DMSO as an oxidant in the presence of an electrophilic activator. Swern oxidations tend to give higher yields and simpler workup; however, they typically employ cryogenic conditions |
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