Reactions of Strained Hydrocarbons with Alkene and Alkyne Metathesis Catalysts

Here we describe the metathesis reactions of a strained eight-membered ring that contains both alkene and alkyne functionality. We find that the alkyne metathesis catalyst produces polymer through a ring-opening alkyne metathesis reaction that is driven by the strain release from the monomer. The strained monomer provides unusual reactivity with ruthenium-based alkene metathesis catalysts. We isolate a discrete trimeric species-a Dewar benzene derivative that is locked in this form through an unsaturated cyclophane strap. Copyright © 2008 American Chemical Society.