🥼organic chemistry review

Metal-Alkylidene Complex

Written by the Fiveable Content Team • Last updated September 2025
Written by the Fiveable Content Team • Last updated September 2025

Definition

A metal-alkylidene complex is a type of organometallic compound where a metal center is bonded to a carbon-based ligand known as an alkylidene. These complexes play a crucial role in olefin metathesis polymerization reactions, which involve the rearrangement of carbon-carbon double bonds.

5 Must Know Facts For Your Next Test

  1. Metal-alkylidene complexes are key intermediates in olefin metathesis polymerization reactions, which are used to synthesize a variety of polymeric materials.
  2. The metal center in a metal-alkylidene complex is typically a transition metal, such as ruthenium, molybdenum, or tungsten, which provides the necessary catalytic activity.
  3. The alkylidene ligand in these complexes is typically derived from an alkene or an alcohol, and it can undergo a series of transformations during the metathesis reaction.
  4. Metal-alkylidene complexes can adopt various geometric configurations, such as trigonal bipyramidal or square pyramidal, depending on the specific metal and ligands involved.
  5. The reactivity and selectivity of metal-alkylidene complexes in olefin metathesis reactions can be tuned by modifying the ligands around the metal center, allowing for the synthesis of a wide range of polymeric materials.

Review Questions

  • Explain the role of metal-alkylidene complexes in olefin metathesis polymerization.
    • Metal-alkylidene complexes are the key intermediates in olefin metathesis polymerization reactions. They serve as the active catalytic species, facilitating the rearrangement of carbon-carbon double bonds in alkene molecules to form new, larger alkene molecules. This process, known as olefin metathesis, is a powerful tool for the synthesis of a variety of polymeric materials, as it allows for the controlled growth of polymer chains through the repeated addition of monomer units.
  • Describe the structural features and properties of metal-alkylidene complexes that enable their catalytic activity in olefin metathesis.
    • Metal-alkylidene complexes typically feature a transition metal center, such as ruthenium, molybdenum, or tungsten, bonded to a carbon-based alkylidene ligand. The specific geometric configuration of the complex, which can be trigonal bipyramidal or square pyramidal, as well as the nature of the other ligands surrounding the metal center, can be tuned to optimize the reactivity and selectivity of the catalyst in olefin metathesis reactions. The ability of the metal-alkylidene complex to undergo a series of transformations, including the formation of metallacyclobutane intermediates, is crucial for the rearrangement of carbon-carbon double bonds during the metathesis process.
  • Evaluate the importance of metal-alkylidene complexes in the broader context of polymer chemistry and materials science.
    • Metal-alkylidene complexes are pivotal in the field of polymer chemistry and materials science, as they enable the synthesis of a wide range of polymeric materials through olefin metathesis polymerization. This versatile reaction allows for the controlled growth of polymer chains, leading to the production of tailored materials with specific properties and applications. The ability to tune the reactivity and selectivity of metal-alkylidene complexes has been instrumental in the development of advanced polymeric materials, such as those used in drug delivery systems, high-performance coatings, and renewable energy technologies. The importance of metal-alkylidene complexes extends beyond their role in olefin metathesis, as they also find applications in other areas of organic synthesis and catalysis, further highlighting their significance in the broader context of chemical research and development.