Se‐Phenyl Prop‐2‐eneselenoate: An Ethylene Equivalent for Diels–Alder Reactions

Reactive: Se-phenyl prop-2-eneselenoate (phenyl selenoacrylate) 2, readily prepared from acryloyl chloride, is a very reactive dienophile in Diels–Alder reactions, and more reactive than acrylates. Its cycloadducts 3 with many dienes 1 can be easily reduced to the hydrocarbons 4 under radical conditions. This process works even in cases where there is an adjacent group that can be easily eliminated, e.g., an allylic ether.