Aromatization and hydrogen-shift of 7-substituted 1,3,5-cycloheptatrienes in the presence of palladium(II) acetate

Article abstract of DOI:10.1248/cpb.41.2187

Reaction of 7-ethoxycarbonyl-1,3,5-cycloheptatriene with palladium(II) acetate afforded 2- and 4-formylbenzoic acid ethyl ester and diethyl maleate via aromatization, and a mixture of position isomers of the cycloheptatriene through hydrogen-shift. The reaction with 7-cyano-1,3,5-cycloheptatriene was also investigated. The reactions are considered to proceed through palladium complexes of the cycloheptatrienes and their norcaradiene isomers.