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.
Carnes
Matthew
M
Department of Chemistry and The Center for Electron Transport in Molecular Nanostructures Columbia University, New York, New York 10027, USA.
Buccella
Daniela
D
Siegrist
Theo
T
Steigerwald
Michael L
ML
Nuckolls
Colin
C
D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003198:Computer Simulation; D018360:Crystallography, X-Ray; D006838:Hydrocarbons / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D008970:Molecular Weight; D009942:Organometallic Compounds / Q000737:chemistry*; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry*
D000475:Alkenes; D000480:Alkynes; D001555:Benzene Derivatives; D006838:Hydrocarbons; D009942:Organometallic Compounds; D011108:Polymers; D012428:Ruthenium