Selective Oxidative Cleavage of the C-C Bond in α,β-Epoxy Ketone into Carbonyl Compounds

Abstract

This method afforded aromatic carbonyl compounds under TBHP via selective oxidative cleavage of the C-C bond in α,β-epoxy ketones. Aromatic acid came from the aroyl section, and aromatic aldehyde came from the other aromatic group. TBHP acted as a free radical initiator and oxidant. The reaction within the solvent went through a ring-opening addition, cleavage of the C-C bond in the ethylene oxide section, and oxidation, affording the target compounds in moderate to good yields. The HPLC yield of aromatic aldehyde was up to 91%. The HPLC yield of aromatic acid was up to 99%. The reaction under solvent-free conditions gave two kinds of aromatic acids coming from different moieties of α,β-epoxy ketone via the further oxidation of aromatic aldehyde. The substituent effect was discussed, and the reaction mechanism was proposed. This method allowed the reaction to occur in a simple system metal-free.