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Acid-Catalyzed Ring-Opening of Epoxides02:24

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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...
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Copper and manganese diazacalix[4]arene complexes: structural and cytotoxicity studies and use in ring opening polymerization of ε-caprolactone and δ-valerolactone.

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Mixed-metal calix[8]arene complexes: structure, and ring opening polymerisation studies.

Tian Xing1, Max Derbyshire2, Mark R J Elsegood2

  • 1Plastics Collaboratory, Department of Chemistry, University of Hull, Cottingham Road, Hull, HU6 7RX, UK. c.redshaw@hull.ac.uk.

Chemical Communications (Cambridge, England)
|June 13, 2022
PubMed
Summary
This summary is machine-generated.

New mixed-metal calixarene systems were synthesized. These systems catalyze the ring-opening polymerization of ε-caprolactone, producing low molecular weight polymers under various conditions.

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Area of Science:

  • Supramolecular Chemistry
  • Organometallic Chemistry
  • Polymer Chemistry

Background:

  • Calixarenes are versatile macrocyclic hosts with tunable properties.
  • Mixed-metal complexes offer unique reactivity and structural diversity.
  • Ring-opening polymerization (ROP) is a key method for synthesizing polyesters.

Purpose of the Study:

  • To synthesize novel mixed-metal calixarene systems.
  • To investigate the catalytic activity of these systems in the ring-opening polymerization of ε-caprolactone.
  • To explore the influence of reaction conditions on polymer properties.

Main Methods:

  • Reaction of group V alkoxides or tungsten oxyalkoxide salts with p-tert-butylcalix[8]areneH8.
  • Characterization of the resulting mixed-metal calixarene complexes.
  • Catalytic polymerization of ε-caprolactone under nitrogen, air, and melt conditions.

Main Results:

  • Formation of intriguing molecular structures of mixed-metal calix[8]arene systems.
  • Demonstration of catalytic activity in ε-caprolactone ROP.
  • Production of mostly low molecular weight polymers across different reaction environments.

Conclusions:

  • Novel mixed-metal calixarene complexes can be effectively synthesized.
  • These complexes exhibit catalytic potential for polyester synthesis.
  • Reaction conditions influence the molecular weight of the resulting polymers.