Lead Tetraacetate Oxidation on Caryachine,A Phenolic Pavine

Lead tetraacetate oxidation on caryachine, a pavine alkaloid possessing a phenolic group at the position para to the N-methine, in dichloromethane yielded four products — 10-acetoxy-O-acetyl-caryachine, 10-acetoxycaryachine, 7-acetoxy-O-acetylcaryachine and (6S, 11R, 12R)-11-acetoxy-O-acetyl-caryachine. The reaction took place via adoption of an acetoxy group at a position majorly ortho to the phenolic group, but very minorly at the desired benzylic position para to the phenolic group.