Oxidative rearrangement of malondialdehyde: substrate scope and mechanistic insights†
Abstract
A novel oxidative rearrangement of malondialdehyde was described. Under the effect of H2O2, malondialdehyde smoothly transferred to carboxylic acid with C–C bond cleavage in good to excellent yields. Mechanistic studies showed that this reaction proceeded via the formation of a 1,2-dioxolane intermediate, followed by concert C–C, O–O, C–H bond cleavage and a hydride shift.