Sodium chromate oxidation of enol benzoates. Allylic oxidation versus a novel rearrangement
Various enol benzoates were oxidized with sodium chromate in acetic acid and acetic anhydride. Allylic oxidation (leading to 1-benzoyloxy-3-oxoalk-1-enes) and a novel oxidative rearrangement (leading to α-benzoyloxyketones) in varying yields were the major reactions observed. The implications of these findings are discussed.