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Related Concept Videos

Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

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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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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...
2.7K
Preparation of Epoxides03:00

Preparation of Epoxides

8.1K
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...
8.1K
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

2.2K
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...
2.2K
Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

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Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain...
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Related Experiment Video

Updated: Sep 13, 2025

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Dispersity-controlled ring-opening polymerization of epoxide.

Yubo Zhou1, Junpeng Zhao2,3, Guangzhao Zhang1

  • 1Faculty of Materials Science and Engineering, South China University of Technology, Guangzhou, PR China.

Nature Communications
|July 27, 2025
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Summary
This summary is machine-generated.

This study introduces a new method to control polymer properties by precisely tuning molar mass distribution in ring-opening polymerization. This approach allows for tailored polymer characteristics through a simple, editable chain-transfer reaction.

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Molar mass distribution (ĐM) significantly impacts polymer properties.
  • Precise control over ĐM in ring-opening polymerization (ROP) remains a significant challenge.
  • Aliphatic polyethers like poly(ethylene oxide) and poly(propylene oxide) are crucial industrial polymers.

Purpose of the Study:

  • To develop a facile method for tailoring the ĐM of aliphatic polyethers.
  • To achieve independent control over ĐM, molar mass, and end-group functionality.
  • To explore the mechanism of chain transfer in organocatalyzed ROP.

Main Methods:

  • Organocatalyzed ring-opening polymerization (ROP) of epoxides.
  • Introduction of a trifluoroacetate chain-transfer agent (CTA).
  • Systematic variation of feed ratios to modulate polymerization outcomes.

Main Results:

  • Achieved triple control over ĐM (1.05-2.00), molar mass (3.6-17.7 kg mol⁻¹), and end-group.
  • Demonstrated non-uniform polymer chain growth with complete initiation efficiency.
  • Confirmed orthogonality between chain growth and transesterification for independent ĐM control.

Conclusions:

  • A simple and effective strategy for controlling ĐM in ROP of epoxides has been established.
  • The trifluoroacetate CTA enables tunable polymer properties through editable chain transfer.
  • This three-modular ROP approach offers precise control over polymer architecture.