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Related Concept Videos

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

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...
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...
β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

β-Dicarbonyl Compounds via Crossed Claisen Condensations

Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds. The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...

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Updated: Jul 2, 2026

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
08:12

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

Ring-opening polymerization of cyclic esters by cyclodextrins.

Akira Harada1, Motofumi Osaki, Yoshinori Takashima

  • 1Department of Macromolecular Science, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan. harada@chem.sci.osaka-u.ac.jp

Accounts of Chemical Research
|August 12, 2008
PubMed
Summary
This summary is machine-generated.

Cyclodextrins (CDs) act as catalysts and structural supports, mimicking enzymes to enable solvent-free polymerization of cyclic esters. This biomimetic approach yields biodegradable polyesters efficiently and sustainably.

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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

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Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers
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Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers

Published on: June 20, 2019

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Last Updated: Jul 2, 2026

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

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Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers
11:42

Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers

Published on: June 20, 2019

Area of Science:

  • Polymer Chemistry
  • Green Chemistry
  • Biomimetic Catalysis

Background:

  • Traditional synthetic polymers face environmental challenges due to harsh reaction conditions and organic solvents.
  • Existing green methods like aqueous polymerization risk polymer hydrolysis, while bulk polymerizations are difficult to control.
  • Nature utilizes enzymes in aqueous or condensed phases to synthesize biopolymers, employing unique structures to manage chain growth.

Purpose of the Study:

  • To develop a novel, environmentally friendly catalytic system for polymer synthesis.
  • To mimic biological polymerization strategies using synthetic catalysts.
  • To investigate cyclodextrins (CDs) as catalysts for the polymerization of cyclic esters.

Main Methods:

  • Utilized cyclodextrins (CDs) as catalysts for the bulk polymerization of cyclic esters (lactones and lactides).
  • Investigated the dual role of CDs as initiators and supporting architectures, similar to chaperone proteins.
  • Analyzed the polymerization process for monomer specificity and the mechanism of monomer insertion.

Main Results:

  • CDs successfully initiated and catalyzed the polymerization of cyclic esters in bulk, yielding high product amounts without solvents or water.
  • CDs acted as structural supports, encircling the growing polymer chain to maintain conformation and prevent aggregation.
  • The system demonstrated high monomer specificity and a unique catalytic mechanism involving initial monomer inclusion and subsequent activation.

Conclusions:

  • Cyclodextrins provide an effective biomimetic system for synthesizing biodegradable polyesters under mild, solvent-free conditions.
  • This approach offers a sustainable alternative to conventional polymer synthesis, aligning with green chemistry principles.
  • The findings present a novel route for producing functional biodegradable polymers by mimicking natural enzymatic polymerization strategies.