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Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

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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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Cationic Chain-Growth Polymerization: Mechanism00:57

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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...
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Free-Radical Chain Reaction and Polymerization of Alkenes02:35

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The conversion of alkenes to macromolecules called polymers is a reaction of high commercial importance. The structure of the polymer is defined by a repeating unit, while the terminal groups are considered insignificant. The average degree of polymerization represents the number of repeating units in the polymer molecule and is denoted by the subscript n.
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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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Electrophilic Addition to Alkynes: Halogenation02:38

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Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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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.
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A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
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C-H Functionalization and Allylic Amination for Post-Polymerization Modification of Polynorbornenes.

Sean R Gitter1, Wei Pin Teh2, Xuejin Yang1

  • 1Department of Chemistry, University of Wisconsin, 53706, Madison, WI, USA.

Angewandte Chemie (International Ed. in English)
|March 21, 2023
PubMed
Summary

A new metal-free selenium-catalyzed method enables efficient post-polymerization modification of polynorbornenes. This direct C-H functionalization preserves polymer backbone alkenes, offering tunable properties and diverse functionalities.

Keywords:
CatalysisC−H FunctionalizationMetathesis PolymersPolymersUpcycling

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Post-polymerization modification (PPM) is crucial for creating advanced polymer materials.
  • Direct C-H functionalization offers a powerful route for efficient polymer modification.
  • Polynorbornenes (PNBs) are versatile polymers produced via ring-opening metathesis polymerization.

Purpose of the Study:

  • To develop a metal-free catalytic system for direct C-H functionalization of PNBs.
  • To explore the application of selenium-catalyzed allylic C-H amination for PPM.
  • To achieve controlled functionalization and tune the properties of modified PNBs.

Main Methods:

  • Ring-opening metathesis polymerization (ROMP) to synthesize PNBs.
  • Selenium-catalyzed direct C-H allylic amination using various aryl sulfonamides.
  • Characterization of polymer structures and properties using spectroscopic and thermal analysis techniques.

Main Results:

  • Efficient metal-free PPM of PNBs was achieved via Se-catalyzed allylic C-H amination.
  • The method preserved alkene groups and avoided double bond transposition in the polymer backbone.
  • Good control over the degree of functionalization and access to diverse polymer functionalities were demonstrated.
  • Tunable thermal properties of the resulting functionalized polymers were observed.

Conclusions:

  • Selenium-catalyzed allylic C-H amination is an effective strategy for the PPM of PNBs.
  • This approach provides a versatile platform for synthesizing functional polymers with tailored properties.
  • The metal-free nature and preservation of backbone integrity make this method highly attractive for polymer synthesis.