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 degrees 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.