Research On Oxidative Rearrangement Of α, β-unsaturated Aldimines With Oxone And AlCl₃ And Ring Opening Of α,β-epoxy Phenyl Ketones With Cerium Ammonium Nitrate (CAN) And KBr

This paper consists of two parts.The first part presents an oxidative rearrangement ofα,β-unsaturated aldimines with Oxone and AlCl₃.The second one provides a ring opening ofα,β-epoxy phenyl ketones with CAN and KBr.The first part Open with a brief introduction to reaction of Oxone as an effective inorganic oxidant with epoxides and others.Our research found thatα,β-unsaturated imines were oxidized toα,β-unsaturated amides by Oxone in the presence of AlCl₃ as a Lewis acid in CH₂Cl₂.Compared with An's findings,the two works have different selectivities.The present reaction lead to the transformation ofα,β-unsaturated aliphatic imine to amides,whereas An's reaction converts simple imines to amides.The second part Simply introduces CAN used as a single electron oxidant in organic oxidation reactions.It was found that ring opening reaction ofα,β-epoxy phenyl ketones were achieved cooperatively using cerium ammonium nitrate(CAN) and potassium bromide.The reaction occurred regioselectively at theβ-C to afford synβ-bromo-α-hydroxyl ketones as main outcomes.Although the reaction mechanism is far from clear,it appears that the present reaction undergoes a free radical initiative ring opening mechanism rather than a one-electron transfer reaction.