REGIOSELECTIVE OXIDATION OF INTERNAL OLEFINS BEARING NEIGHBORING OXYGEN FUNCTIONS BY MEANS OF PALLADIUM CATALYSTS. PREPARATION OF β-ALKOXY OR ACETOXY KETONES FROM ALLYL AND HOMOALLYL ETHERS OR ESTERS

Article abstract of DOI:10.1016/S0040-4039(00)87430-4

A new preparative method of β- and γ-alkoxy (acetoxy) ketones, which are important precursors of vinyl ketones and 1,4-diketones, respectively, is presented.With PdCl2/CuCl/O2 or PdCl2/p-benzoquinone catalyst system, internal olefins bearing allylic alkoxy or acetoxy group underwent regioselective oxidation to form the corresponding β-alkoxy or β-acetoxy ketones.Similarly, γ-acetoxy ketones were obtained from homoallyl acetates having internal olefins with high regioselectivity.