Kornblum oxidation

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Kornblum oxidation
Named after Nathan Kornblum
Reaction type Organic redox reaction

The Kornblum oxidation, named after

carbonyl compounds.[1][2][3]

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.

References

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  5. ^ a b Kürti, László; Czakó, Barbara (2005). Strategic Applications of Named Reactions in Organic Synthesis: Background and Detailed Mechanisms. pp. 250–251.