Reactions of 2,6-Dibenzylidenecyclohexanone and its Derivatives in High-Temperature Water

The reactivity of derivatives of 2,6-dibenzylidenecyclohexanone was investigated in water at 220–250◦C under microwave conditions, without added catalyst. Retro-Claisen–Schmidt processes predominated. Hydrolytic attack at the benzylic position afforded a 2-benzylidenecyclohexanone derivative and liberated an aryl aldehyde. Dienones substituted with electron-withdrawing or-donating groups on the aryl rings were more susceptible to hydrolysis than was the parent 2,6-dibenzylidenecyclohexanone