ArticleJournal of the American Chemical Society2010
Scope of the ring-opening metathesis polymerization (ROMP) reaction of 1-substituted cyclobutenes.
Article in Journal of the American Chemical Society, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed, 85 citations in OpenAlex.
- Stretching decelerates ring-opening metathesis at cis-olefins in stressed molecular bows.Nature communications · 2026Article
- Ring-Opening Metathesis Polymerization of 1,2-Dihydroazete Derivatives.Angewandte Chemie (International ed. in English) · 2025Article
- Tricyclononenes and tricyclononadienes as efficient monomers for controlled ROMP: understanding structure-propagation rate relationships and enabling facile post-polymerization modification.Chemical science · 2024Article
- Ring-Opening Metathesis Polymerization of the Dewar Isomer of 1,2-Azaborinine, a B-N Isostere of Benzene.ACS macro letters · 2024Article
- Strain-Inducing Positional Alkene Isomerization.Journal of the American Chemical Society · 2023Article
- Sequence-Controlled Polymers Through Entropy-Driven Ring-Opening Metathesis Polymerization: Theory, Molecular Weight Control, and Monomer Design.Journal of the American Chemical Society · 2019Article
- Access to Bicyclo[4.2.0]octene Monomers To Explore the Scope of Alternating Ring-Opening Metathesis Polymerization.The Journal of organic chemistry · 2018Article
- Ring-Opening Metathesis Polymerization of Butyl SubstitutedACS macro letters · 2017Article
- Precision Synthesis of Alternating Copolymers via Ring-Opening Polymerization of 1-Substituted Cyclobutenes.Accounts of chemical research · 2016Article
- Ru-Catalyzed Isomerization Provides Access to Alternating Copolymers via Ring-Opening Metathesis Polymerization.Macromolecules · 2015Article
- Alternating ROMP copolymers containing charge-transfer units.ACS macro letters · 2013Article
- Synthesis of highly cis, syndiotactic polymers via ring-opening metathesis polymerization using ruthenium metathesis catalysts.Journal of the American Chemical Society · 2013Article
- Antibacterial studies of cationic polymers with alternating, random, and uniform backbones.ACS chemical biology · 2011Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
The reactivities of a series of 1-substituted cyclobutene derivatives (carboxylate esters, carboxamides, and carbinol esters) were investigated as substrates for ring-opening metathesis polymerization (ROMP) with [(H(2)IMes)(3-Br-pyridine)(2)(Cl)(2)Ru=CHPh]. Both the secondary amides of 1-cyclobutenecarboxylic acid and the esters of 1-cyclobutene-1-methanol undergo polymerization. The secondary amides provide translationally invariant polymers (E-olefins). Although the carbinol esters yield stereo- and regiochemically heterogeneous polymers, the 1-cyclobutenecarboxylic acid esters and tertiary amides undergo ring-opening metathesis (ROM) but not ROMP. The regio- and stereochemical outcomes of these ROMP and ROM reactions were analyzed at the B3LYP/6-31G* and LANL2DZ levels of theory. Calculations suggest that the regiochemistry and stereochemistry of the addition to the propagating carbene to form the metallocyclobutane intermediate depend on both charge distribution and steric interactions.
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Registered trials
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