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.