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Ring Closing Metathesis: Comparison
Please note this is a comparison between Version 3 by Helena Kang and Version 2 by Helena Kang.

Ring-closing metathesis (RCM) is an intramolecular olefin metathesis in which two alkene units of the same molecule exchange alkylidene fragments at a metal–carbene catalyst to produce a cyclic alkene and a volatile olefin, typically ethylene [1]. In advanced synthetic organic chemistry the concept is bounded by the intramolecular pairing of the two alkenes and by the metathesis elementary steps of (2+2) cycloaddition and cycloreversion. Essential features are a diene (or enyne) substrate whose tether length sets the ring size, a well-defined ruthenium, molybdenum, or tungsten alkylidene catalyst, and an equilibrium that is driven toward the cycle by removal of the small-olefin byproduct [2]. RCM constructs five- to medium-sized rings and macrocycles, including oxygen- and nitrogen-containing heterocycles, when the tether geometry permits productive approach of the two olefins [1][3]. The transformation is distinguished from ring-opening metathesis by the direction of the equilibrium (cycle-forming versus cycle-opening) and from intermolecular cross-metathesis by the unimolecular connection of the two reacting alkenes. Conceptual limits exclude metal-catalyzed cyclizations that proceed by oxidative cyclization or radical addition rather than by alkylidene exchange.

  • ring-closing metathesis
  • metal alkylidene
  • cyclic alkene
  • intramolecular metathesis

References

  1. Alexander Deiters; Stephen F. Martin; Synthesis of Oxygen- and Nitrogen-Containing Heterocycles by Ring-Closing Metathesis. Chem. Rev. 2004, 104, 2199-2238. [CrossRef]
  2. Sebastien Monfette; Deryn E. Fogg; Equilibrium Ring-Closing Metathesis. Chem. Rev. 2009, 109, 3783-3816. [CrossRef]
  3. Martin E. Maier; Synthesis of Medium-Sized Rings by the Ring-Closing Metathesis Reaction. Angew. Chem. Int. Ed. 2000, 39, 2073-2077. [CrossRef]
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