Suspension Ring-Opening Metathesis Polymerization: The Preparation of Norbornene-Based Resins for Application in Organic Synthesis
- 9 April 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (10), 3319-3329
- https://doi.org/10.1021/jo049827s
Abstract
A series of norbornene-based resin beads were obtained by aqueous suspension ring-opening metathesis polymerization (ROMP) and used as polymeric supports for organic synthesis. These resins were prepared from norbornene, norborn-2-ene-5-methanol, and cross-linkers such as bis(norborn-2-ene-5-methoxy)alkanes, di(norborn-2-ene-5-methyl)ether, and 1,3-di(norborn-2-ene-5-methoxy)benzene. The resulting unsaturated ROMP (U-ROMP) resins containing olefin repeat units were chemically modified using hydrogenation, hydrofluorination, chlorination, and bromination reactions to produce saturated ROMP resins with different chemical and physical properties. The hydrogenated ROMP (H-ROMP) resin was found to be highly resistant to acidic, basic, Lewis acid, and Birch reduction conditions and was assessed as a polymeric support in a series of solid-phase synthetic applications. The H-ROMP resin was found to have superior performance compared to polystyrene-divinylbenzene (PS-DVB) copolymers in aromatic nitration and acylation reactions. In a conventional five-step solid-phase synthesis of a hydantoin, similar results were obtained for both the H-ROMP and PS-DVB resins. The U-ROMP resin was also shown to be effective in the solid-phase syntheses of benzimidazoles and benzimidazolones.Keywords
This publication has 29 references indexed in Scilit:
- Dispersion Ring-Opening Metathesis Polymerization of Norbornene Using PEO-Based StabilizersMacromolecules, 2002
- Synthesis of Well-Defined Poly((vinyl alcohol)2-alt-methylene) via Ring-Opening Metathesis PolymerizationMacromolecules, 2002
- Aqueous Catalytic Polymerization of OlefinsAngewandte Chemie-International Edition, 2002
- Ring-Opening Metathesis Polymerization in EmulsionMacromolecules, 2001
- A Series of Well‐Defined Metathesis Catalysts–Synthesis of [RuCl2(CHR′)(PR3)2] and Its ReactionsAngewandte Chemie-International Edition, 1995
- Eine Molybdän‐Phosphor‐Dreifachbindung: Synthese, Struktur und Reaktivität von [Mo(P)(NRAr)3], einem Komplex mit terminalem PhosphidoligandenAngewandte Chemie, 1995
- Novel method for monitoring the coupling efficiency in solid phase peptide synthesis*International Journal of Peptide and Protein Research, 1988
- Chiral biphenyl bis(crown ethers): synthesis and resolutionThe Journal of Organic Chemistry, 1987
- Silane reductions in acidic media. 10. Ionic hydrogenation of cycloalkenes. Stereoselectivity and mechanismThe Journal of Organic Chemistry, 1978
- Polynorbornene by Coördination Polymerization1Journal of the American Chemical Society, 1960