Reactions of strained hydrocarbons with alkene and alkyne metathesis catalysts

J Am Chem Soc. 2008 Oct 29;130(43):14078-9. doi: 10.1021/ja806351m. Epub 2008 Oct 1.

Abstract

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.

MeSH terms

  • Alkenes / chemistry*
  • Alkynes / chemistry*
  • Benzene Derivatives / chemical synthesis*
  • Benzene Derivatives / chemistry
  • Catalysis
  • Computer Simulation
  • Crystallography, X-Ray
  • Hydrocarbons / chemistry*
  • Models, Chemical
  • Molecular Structure
  • Molecular Weight
  • Organometallic Compounds / chemistry*
  • Polymers / chemical synthesis
  • Polymers / chemistry
  • Ruthenium / chemistry*

Substances

  • Alkenes
  • Alkynes
  • Benzene Derivatives
  • Hydrocarbons
  • Organometallic Compounds
  • Polymers
  • Ruthenium