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Related Concept Videos

Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

10.5K
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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Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

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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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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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

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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...
3.2K
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

2.7K
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.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
2.7K
Preparation of Epoxides03:00

Preparation of Epoxides

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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

2.3K
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...
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Updated: Mar 1, 2026

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Metathesis-Sourced Epoxides in Ring-Opening Copolymerization: Selective Access to Degradable Polythioesters.

Niracha Tangyen1,2, Bhargav R Manjunatha1, Valerio D'Elia2,3

  • 1Makromolekulare Chemie, Universität Bayreuth, Bayreuth, Germany.

Macromolecular Rapid Communications
|February 28, 2026
PubMed
Summary

New cyclopentene epoxides enable controlled synthesis of degradable polyesters and polythioesters through ring-opening copolymerization. These versatile monomers offer precise control over polymer structure and properties.

Keywords:
metathesismolybdenumpolythioestersring‐opening copolymerization

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Controlled synthesis of degradable polymers is crucial for sustainable materials.
  • Ring-opening copolymerization (ROCOP) offers a pathway to well-defined polymer architectures.
  • Development of novel monomers is key to expanding ROCOP capabilities.

Purpose of the Study:

  • To synthesize novel ester-substituted cyclopentene epoxides.
  • To investigate their utility as monomers in controlled ring-opening copolymerization (ROCOP).
  • To produce well-defined degradable polyesters and polythioesters.

Main Methods:

  • Synthesis of cyclopentene epoxides via ring-closing metathesis and epoxidation.
  • Ring-opening copolymerization (ROCOP) with phthalic thioanhydride (PTA) and phthalic anhydride (PA).
  • Optimization of monomer purity, catalyst preparation, and reaction conditions.

Main Results:

  • Selective access to monomers for controlled ROCOP achieved.
  • Fully alternating PTA/epoxide ROCOP yielded well-defined poly(ester-alt-thioester)s (Mw up to ~38 kg/mol).
  • Successful phthalic anhydride (PA) ROCOP and selective terpolymerizations demonstrated; substituent variation confirmed scaffold robustness.

Conclusions:

  • Metathesis-derived cyclopentene epoxides are versatile and accessible monomers.
  • These monomers enable controlled synthesis of degradable polyesters and polythioesters.
  • The study establishes a new route to advanced degradable polymer materials.