Parikh-Doering oxidation

What is Parikh-Doering oxidation?

The Parikh-Doering oxidation is a reaction that oxidizes primary and secondary alcohols into aldehydes and ketones at room temperature. This reaction was first reported in 1967 and is named after Parikh and Doering. The oxidation is carried out using a sulfur trioxide-pyridine complex SO3·Py in combination with dimethylsulfoxide DMSO and triethylamine NEt3.

Parikh-Doering oxidation - general reaction scheme - Parikh-Doering protocol - Doering oxidation
Parikh-Doering oxidation

The Parikh-Doering oxidation is fast, usually completed within minutes, and has convenient working conditions. It is also tolerant of functional groups and produces negligible side products. The oxidation is flexible and can be charged with more reagent if necessary. The reaction has been proven to be effective for the oxidation of alcohols mounted onto polymer and in the preparation of α,β-unsaturated carbonyl compounds. However, it is not suitable for highly strained alcohols.

The Parikh-Doering oxidation is also known as the Parikh-Doering protocol or Doering oxidation, and has been shown to be superior to TPAP/NMO oxidation, but not as effective as the Moffatt-Swern oxidation and Corey-Suggs oxidation for the oxidation of long-chain alcohols.

References

Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxide
Jekishan R. Parikh and William v. E. Doering
Journal of the American Chemical Society 1967 89 (21), 5505-5507
DOI: 10.1021/ja00997a067

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