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Related Concept Videos

Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

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,...
Anionic Chain-Growth Polymerization: Mechanism01:04

Anionic Chain-Growth Polymerization: Mechanism

The mechanism for anionic chain-growth polymerization involves initiation, propagation, and termination steps. In the initiation step, a nucleophilic anion, such as butyl lithium, initiates the polymerization process by attacking the π bond of the vinylic monomer. As a result, a carbanion, stabilized by the electron‐withdrawing group, is generated. The resulting carbanion acts as a Michael donor in the propagation step and attacks the second vinylic monomer, which acts as a Michael acceptor.
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

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 generated carbocation,...
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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...

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Isobutene polymerization using a chelating diborane co-initiator.

Stewart P Lewis1, Nicholas J Taylor, Warren E Piers

  • 1Department of Polymer Science, University of Akron, Akron, OH 44325-3909, USA.

Journal of the American Chemical Society
|December 4, 2003
PubMed
Summary

Lewis acidic diborane is effective for isobutene polymerization. It forms stable ion pairs with alkyl chlorides and ethers, which can further react at higher temperatures.

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Area of Science:

  • Organometallic Chemistry
  • Polymer Chemistry

Background:

  • Lewis acidic diborane is a potent initiator for isobutene polymerization.
  • Understanding the reaction mechanisms of diborane with electrophilic species is crucial for controlling polymerization.

Purpose of the Study:

  • To investigate the reaction pathways of Lewis acidic diborane with cumyl chloride and cumyl methyl ether.
  • To characterize the intermediate species formed during these reactions using advanced spectroscopic techniques.

Main Methods:

  • Variable-temperature 1H and 19F Nuclear Magnetic Resonance (NMR) spectroscopy were employed.
  • X-ray crystallography was utilized to determine the structure of specific ion pairs.

Main Results:

  • Stable ion pairs (2a, 2b) are formed at low temperatures between diborane and electrophilic reagents.
  • At elevated temperatures, these ion pairs undergo cyclization to form phenyl-1,3,3-trimethylindan (3) or anion degradation.
  • Reaction with Ph3C-Cl generated a unique ion pair (4) with a weakly associated mu-Cl counteranion.

Conclusions:

  • Diborane's Lewis acidity facilitates the formation of reactive ion pairs.
  • The observed reactions highlight the complex mechanistic pathways involving diborane in cationic polymerization initiation.