Kornblum oxidation
Kornblum oxidation | |
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Named after | Nathan Kornblum |
Reaction type | Organic redox reaction |
The Kornblum oxidation, named after
Mechanism
Similar to sulfonium-based oxidation of alcohols to aldehydes reactions, the Kornblum oxidation creates an alkoxysulphonium ion, which, in the presence of a base, such as triethylamine (Et3N), undergoes an elimination reaction to form the aldehyde or ketone.
Extensions
The first step is an
benzylic and α-halo ketones. To increase the range of viable substrates, Kornblum later added a preliminary conversion of the halide to a tosylate, which is a better leaving group, to the protocol, and using pyridine-N-oxide or similar reagents rather than DMSO.[5] The Ganem oxidation
built on this latter modification, expanding on the use of various N-oxide reagents.