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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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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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Base-Catalyzed Ring-Opening of Epoxides02:26

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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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Preparation of Epoxides03:00

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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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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: Acyclic Diene Metathesis (ADMET)00:53

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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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A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
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Acetal-Based Functional Epoxide Monomers: Polymerizations and Applications.

Jinsu Baek1, Minseong Kim1,2, Youngsin Park1

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

Macromolecular Bioscience
|August 9, 2021
PubMed
Summary
This summary is machine-generated.

Protecting groups, like acetals, are crucial for functional monomers in anionic ring-opening polymerization (AROP). These acetal-based monomers enable new pH-responsive polyethers for biomedical uses.

Keywords:
acetalsepoxide monomerspolyethers

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Area of Science:

  • Organic Chemistry
  • Polymer Science
  • Materials Science

Background:

  • Anionic ring-opening polymerization (AROP) requires protecting groups due to harsh reaction conditions incompatible with most functional groups.
  • Acetal-based protecting groups have emerged as a key strategy for synthesizing functional monomers in AROP.
  • Ethyoxyethyl glycidyl ether is a representative example, paving the way for advanced acetal monomers.

Purpose of the Study:

  • To review recent advancements in acetal-based monomers for functional polyethers.
  • To highlight the synthesis, polymerization, and applications of these monomers.
  • To explore their dual role as protecting groups and pH-responsive moieties.

Main Methods:

  • Development of novel acetal-protected epoxide monomers.
  • Anionic ring-opening polymerization (AROP) techniques.
  • Characterization of resulting polyethers and assessment of their properties.

Main Results:

  • Acetal-based monomers are effectively polymerized via AROP, yielding functional polyethers.
  • These polyethers exhibit pH-responsive behavior, making them suitable for biomedical applications.
  • The protecting group strategy allows for the incorporation of diverse functionalities.

Conclusions:

  • Acetal-based monomers represent a versatile platform for creating advanced functional polyethers.
  • Their application extends beyond protecting groups to enabling smart materials for biomedical use.
  • Continued research in this area promises further innovation in polymer chemistry.