Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

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,...
Radical Chain-Growth Polymerization: Chain Branching01:17

Radical Chain-Growth Polymerization: Chain Branching

The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from the...
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
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.
Radical Chain-Growth Polymerization: Mechanism01:09

Radical Chain-Growth Polymerization: Mechanism

The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this species into the...
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,...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Preoperative Disc Height as a Prognostic Factor in Laminoplasty for Cervical Spondylotic Myelopathy with Degenerative Spondylolisthesis.

Spine surgery and related research·2026
Same author

Electrolyte-anion-controlled reactivity of aromatic radical cations.

Chemical science·2026
Same author

Precisely Controlled Electrochemical Phosphonylation: Tailoring π-Conjugated Polymer Properties for High-Performance Organic Electrochemical Transistors.

Angewandte Chemie (International ed. in English)·2026
Same author

Replication of the Association between Retinal Aging Clock Susceptibility Genes and Retinal Age Gap in an Asian Population: The Nagahama Study.

Ophthalmology science·2026
Same author

Risk of Glaucoma and Undergoing Glaucoma Surgery in Myopic and Highly Myopic Eyes: A Nationwide Population-Based Cohort Study.

Ophthalmology·2026
Same author

Clinical Accuracy and Length of Percutaneous Pedicle Screw (PPS) Insertion in the Thoracic and Lumbar Spine Under Two-Dimensional Fluoroscopy: A Comparative Study of PPS Placement With Guidewireless and Conventional Guidewire Systems.

Cureus·2025

Related Experiment Video

Updated: Jun 23, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Prins-type polymerization using ionic liquid hydrogen fluoride salts.

Shinsuke Inagi1, Yuta Doi, Yuichiro Kishi

  • 1Department of Electronic Chemistry, Tokyo Institute of Technology, Yokohama, Japan.

Chemical Communications (Cambridge, England)
|May 14, 2009
PubMed
Summary
This summary is machine-generated.

Researchers developed a novel Prins-type polymerization method to create unique 4-fluorinated tetrahydropyran polymers with high stereoselectivity. This breakthrough offers new possibilities for advanced polymer materials.

More Related Videos

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
06:55

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level

Published on: September 26, 2016

Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers
11:42

Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers

Published on: June 20, 2019

Related Experiment Videos

Last Updated: Jun 23, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
06:55

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level

Published on: September 26, 2016

Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers
11:42

Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers

Published on: June 20, 2019

Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Stereoselective polymerization is crucial for developing polymers with tailored properties.
  • Tetrahydropyran rings are valuable structural motifs in various functional materials.
  • Fluorinated polymers offer unique characteristics, including thermal stability and chemical resistance.

Purpose of the Study:

  • To report the first successful application of Prins-type polymerization for synthesizing 4-fluorinated tetrahydropyran-containing polymers.
  • To achieve high stereoselectivity in the polymerization process.
  • To explore the potential of this method for creating novel fluorinated polymers.

Main Methods:

  • Prins-type cyclization polymerization initiated by Lewis or Brønsted acids.
  • Utilizing specific monomers containing fluorinated precursors for tetrahydropyran ring formation.
  • Characterization of polymer microstructure and stereochemistry using NMR spectroscopy and other analytical techniques.

Main Results:

  • Successful synthesis of 4-fluorinated tetrahydropyran-containing polymers via Prins-type polymerization.
  • Demonstration of high stereoselectivity, leading to polymers with controlled stereochemistry.
  • Characterization confirmed the successful incorporation of the fluorinated tetrahydropyran units.

Conclusions:

  • Prins-type polymerization is a viable and effective method for stereoselective synthesis of 4-fluorinated tetrahydropyran polymers.
  • This study expands the synthetic toolbox for creating advanced fluorinated polymers.
  • The developed polymers hold potential for applications in areas requiring high-performance materials.