14772-40-8Relevant articles and documents
Epoxidation and Baeyer-Villiger Oxidation of γ-Hydroxy-αβ-unsaturated Ketones on Exposure to m-Chloroperbenzoic Acid
Medelovici, Marioara,Glotter, Erwin
, p. 1735 - 1740 (2007/10/02)
Treatment of 3β- and 3α-hydroxy-(acetoxy-)cholest-4-en-6-one and of 6β- and 6α-hydroxy-(acetoxy-)cholest-4-en-3-one with MCPBA gives two types of product, depending on the initial site of the peroxy acid attack.Attack at the carbonyl group gives a Baeyer-Villiger rearrangement leading first to enol lactones and then by epoxidation of the latter to epoxy lactones.Alternatively, attack at the double bond gives epoxy ketones which can subsequently undergo a Baeyer-Villiger rearrangement leading to epoxy lactones.With one exception (3α-hydroxycholest-4-en-6-one), the Baeyer-Villiger oxidation of the enone is the dominant process.Epoxidation of the double bond is suppressed in the presence of an axial 3α- or 6β-acetoxy group.