"Dual Activity of Ruthenium Catalysts in Controlled Radical Reactions And Olefin Metathesis"

Lionel Delaude, Sébastien Delfosse, Albert Demonceau, Aurore Richel, and Alfred F. Noels

           title: Novel Metathesis Chemistry: Well-Defined Initiator
                  Systems for Specialty Chemical Synthesis, Tailored
                  Polymers and Advanced Material Applications
          series: NATO Science Series II. Mathematics, Physics and Chemistry
          editor: Yavuz Imamoglu and Lajos Bencze
       publisher: Kluwer
            city: Dordrecht
            year: 2003
          volume: 122
      first page: 87
       last page: 100
            isbn: 978-1-4020-1570-0 (Print) 978-94-010-0066-6 (Online)
             doi: 10.1007/978-94-010-0066-6_7

Abstract: The catalytic activity of five ruthenium-arene complexes of the RuCl₂(p-cymene)L type was investigated in controlled radical reactions and olefin metathesis. The ligands L were stable N-heterocyclic carbenes (NHCs) derived from imidazol-2-ylidene. They differed by the nature of the substituents on the nitrogen atoms (R¹) and on the carbon-carbon double bond (R²) of the heterocyclic ring. Thus, R¹ was either the mesityl or the cyclohexyl group, and R² included methyl, hydrogen, or chloro substituents. The complexes were tested as initators for the Atom Transfer Radical Addition (ATRA) of carbon tetrachloride to methyl methacrylate and styrene, for the Atom Transfer Radical Polymerization (ATRP) of methyl methacrylate and styrene, and for the Ring-Opening Metathesis Polymerization (ROMP) of cyclooctene. Some species displayed a dual activity and promoted both olefin metathesis and ATRP.

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