Abstract
Reaction of alkyl, acetoxy, and silyl enol ethers of 3-(organosilyl) cyclohexanone with molecular dioxygen in toluene at 110 °C produced the corresponding conjugated enones in yields up to 88% yield. The reaction of the same type failed on replacement of the silyl group at the C-3 position with an isopropyl group. These results indicate the existence of an unprecedented silicon-induced ene-type reaction. Its reaction mechanism, generality, limitations, and exceptions are discussed. © 2008 American Chemical Society.