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Related Concept Videos

Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

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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Ring-opening polymerization of cyclic esters with lithium amine-bis(phenolate) complexes.

Rebecca K Dean1, Amy M Reckling, Hua Chen

  • 1Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland A1B 3X7, Canada.

Dalton Transactions (Cambridge, England : 2003)
|January 3, 2013
PubMed
Summary
This summary is machine-generated.

New lithium compounds with amino-bis(phenolato)-tetrahydrofuranyl ligands were synthesized and characterized. These lithium complexes show reactivity in the ring-opening polymerization of rac-lactide, with factors influencing the process being studied.

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Area of Science:

  • Organometallic Chemistry
  • Polymer Chemistry
  • Materials Science

Background:

  • Lithium compounds with tetradentate ligands are of interest for catalytic applications.
  • Amino-bis(phenolato) ligands offer versatile coordination environments for metal centers.
  • Tetrahydrofuranyl groups can influence the solubility and reactivity of organometallic complexes.

Purpose of the Study:

  • To synthesize and characterize novel lithium compounds featuring tetradentate amino-bis(phenolato)-tetrahydrofuranyl ligands.
  • To investigate the structural properties of these lithium complexes using multinuclear NMR and X-ray diffraction.
  • To evaluate the efficacy of these complexes as initiators for the ring-opening polymerization of rac-lactide.

Main Methods:

  • Synthesis of lithium complexes Li(2)[L1], Li(2)[L2], Li(2)[L3], and Li(2)[L4].
  • Characterization using multinuclear solution NMR ((1)H, (13)C, (6)Li, (7)Li) and solid-state NMR spectroscopy.
  • Structural determination via single-crystal X-ray diffraction for selected complexes and their pyridine adduct.
  • Ring-opening polymerization (ROP) studies of rac-lactide using the synthesized lithium complexes.

Main Results:

  • Successful synthesis and full characterization of four novel dilithium complexes.
  • Structural elucidation of complexes 3, 4, and 5, revealing coordination modes and steric influences.
  • Demonstrated catalytic activity of the lithium complexes in the ROP of rac-lactide.
  • Identified key parameters affecting polymerization, including monomer concentration, monomer/Li ratio, temperature, and time.

Conclusions:

  • The synthesized lithium complexes are effective initiators for rac-lactide polymerization.
  • Ligand structure and reaction conditions significantly influence polymerization outcomes.
  • These findings contribute to the development of new organolithium catalysts for biodegradable polymer synthesis.