Novel allylic oxidation of conjugate ketones with VO(OR)Cl2

Article abstract of DOI:10.1016/S0040-4039(00)74318-8

An oxo group is introduced at the allylic position of 3-methyl-2-cyclopenten-1-one and β-ionone on treatment with VO(OR)Cl₂ in ROH. VO(OR)Cl₂ induces γ-alkoxylation in the case of 2-cyclopenten-1-one. Reaction of 1-acetyl-1-cyclohexene with VO(OEt)Cl₂ results in γ-alkoxylation and/or aromatization to give 1-acetyl-3-ethoxy-1-cyclohexene and the corresponding aromatic.