Parikh–Doering oxidation

The Parikh -Doering oxidation is a name reaction in organic chemistry, which was named after their discoverers Jekishan R. Parikh and William von E. Doering.

The Parikh -Doering oxidation, primary and secondary alcohols to aldehydes or ketones transferred. Here, (DMSO ) was used as the oxidizing agent as in the Swern oxidation -activated dimethyl sulfoxide. To activate However, an adduct of sulfur trioxide and pyridine in the presence of triethylamine serves.

The reaction under mild conditions can be carried out usually at 0 ° C is performed.

Reaction mechanism

In the first step, the dimethyl sulfoxide (DMSO ) is activated by means of sulfur trioxide.

The activated DMSO is nucleophilic attack by the alcohol. The resulting intermediate is then deprotonated by pyridine. In addition, sulfate is cleaved by a rearrangement, which is separated in a complex with the pyridinium. Then the Alkoxysulfoniumion is deprotonated by triethylamine. The ensuing rearrangement within the molecule results in the removal of the sulfur compound, so that the final product, the ketone or aldehyde is formed.