The supramolecular effect of stilbenophanes on the Wacker oxidation progress: A structure–activity relationship study

• The study on Wacker oxidation of stilbenophanes.
• The role of the structural elements of the stilbenophanes on the oxidation.
• High product selectivity is resulted.
• A clear role of host–guest complexation is found.

The Wacker oxidation of cis and trans isomers of two defined stilbenophanes with different alkyl chain lengths gave the corresponding cyclic ketones in different rate. It was found that the oxidation rate of stilbenophanes is in order to: E-1 >> Z-3 ∼ Z-1 > E-3 to show the importance of supramolecular effect of trans isomers in elucidation of the reaction mechanism. Cyclic voltammetry and Uv–Vis measurements showed a different behavior for the complexation of trans isomers with palladium ion to confirm the Wacker oxidation data.

The Wacker oxidation of cis and trans isomers of two defined stilbenophanes with different alkyl chain lengths gave the corresponding cyclic ketones in different rate.Figure optionsDownload as PowerPoint slide