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Reactions of strained hydrocarbons with alkene and alkyne metathesis catalysts.
J Am Chem Soc. 2008 Oct 29; 130(43):14078-9.JA

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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Carnes M
Department of Chemistry and The Center for Electron Transport in Molecular Nanostructures Columbia University, New York, New York 10027, USA.
Buccella D
No affiliation info available
Siegrist T
No affiliation info available
Steigerwald ML
No affiliation info available
Nuckolls C
No affiliation info available

MeSH

AlkenesAlkynesBenzene DerivativesCatalysisComputer SimulationCrystallography, X-RayHydrocarbonsModels, ChemicalMolecular StructureMolecular WeightOrganometallic CompoundsPolymersRuthenium

Pub Type(s)

Journal Article

Language

eng

PubMed ID

18826219

Citation

Carnes, Matthew, et al. "Reactions of Strained Hydrocarbons With Alkene and Alkyne Metathesis Catalysts." Journal of the American Chemical Society, vol. 130, no. 43, 2008, pp. 14078-9.
Carnes M, Buccella D, Siegrist T, et al. Reactions of strained hydrocarbons with alkene and alkyne metathesis catalysts. J Am Chem Soc. 2008;130(43):14078-9.
Carnes, M., Buccella, D., Siegrist, T., Steigerwald, M. L., & Nuckolls, C. (2008). Reactions of strained hydrocarbons with alkene and alkyne metathesis catalysts. Journal of the American Chemical Society, 130(43), 14078-9. https://doi.org/10.1021/ja806351m
Carnes M, et al. Reactions of Strained Hydrocarbons With Alkene and Alkyne Metathesis Catalysts. J Am Chem Soc. 2008 Oct 29;130(43):14078-9. PubMed PMID: 18826219.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Reactions of strained hydrocarbons with alkene and alkyne metathesis catalysts. AU - Carnes,Matthew, AU - Buccella,Daniela, AU - Siegrist,Theo, AU - Steigerwald,Michael L, AU - Nuckolls,Colin, Y1 - 2008/10/01/ PY - 2008/10/2/pubmed PY - 2009/1/29/medline PY - 2008/10/2/entrez SP - 14078 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 130 IS - 43 N2 - 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. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/18826219/Reactions_of_strained_hydrocarbons_with_alkene_and_alkyne_metathesis_catalysts_ L2 - https://doi.org/10.1021/ja806351m DB - PRIME DP - Unbound Medicine ER -