Polonovski Reaction

Abstract

The transformation of a tertiary amine oxide into a N , N ‐disubstituted acetamide and an aldehyde by treatment of the tertiary amine oxide with acetic anhydride or acetyl chloride is generally known as the Polonovski reaction. This reaction is also referred to as the Polonovski transformation. It has been reported that under modified condition this reaction can be stopped at the iminium stage, which can be trapped by the addition of cyanide to form an amino nitrile. This reaction is known as the Polonovski–Potier reaction. It has been found that the elimination occurs via an E2 type mechanism and cis ‐elimination has also been observed for nupharidine‐type alkaloids. This reaction has wide application in the transformation of alkaloids.