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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

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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

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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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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...
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Olefin Metathesis Polymerization: Overview01:13

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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.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists...
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Anionic Chain-Growth Polymerization: Overview01:20

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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
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Anionic ring-opening polymerization of functional epoxide monomers in the solid state.

Jihye Park1, Ahyun Kim1, Byeong-Su Kim2

  • 1Department of Chemistry, Yonsei University, Seoul, 03722, Republic of Korea.

Nature Communications
|September 20, 2023
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Summary
This summary is machine-generated.

Mechanochemical polymerization using ball milling enables solid-state synthesis of polyethers. Monomer melting point is a key predictor of reactivity, with bulkier monomers showing faster conversions.

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Mechanochemistry

Background:

  • Mechanochemical polymerization, particularly via ball milling, offers unique solid-state synthesis pathways.
  • Understanding the specific reactivity and critical parameters governing this process is essential for its advancement.

Purpose of the Study:

  • To investigate the solid-state anionic ring-opening polymerization of functional epoxides using ball milling.
  • To elucidate the critical monomer parameters influencing mechanochemical polymerization reactivity.
  • To establish correlations between monomer properties and polymerization outcomes.

Main Methods:

  • Solid-state anionic ring-opening polymerization.
  • Ball milling technique for mechanochemical synthesis.
  • Characterization using Nuclear Magnetic Resonance (NMR), Gel Permeation Chromatography (GPC), and MALDI-ToF mass spectrometry.

Main Results:

  • Successful synthesis of polyethers from various functional epoxide monomers.
  • Demonstration of controllable polymerization through ball milling.
  • Observation that bulky monomers exhibit faster conversions in solid-state compared to solution polymerization.
  • Identification of a linear correlation between monomer melting point and polymerization conversion.

Conclusions:

  • Monomer melting point is a critical predictor of mechanochemical polymerization reactivity in ball milling.
  • Insights gained facilitate the efficient design and understanding of mechanochemical polymerization processes.
  • This study advances the field of solid-state polymer synthesis via mechanochemistry.