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

Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

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...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

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...

You might also read

Related Articles

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

Sort by
Same author

Mechanisms by Which Plant Extracts Ameliorate Bovine Mastitis Through the Regulation of Mitochondrial Function: A Review.

Cells·2026
Same author

Highly robust underwater wireless optical communication system with optical background rejection and adaptive algorithm under strong artificial illumination.

Optics express·2026
Same author

Covalent Borane-Thiourea Organocatalyst for Stereoselective Ring-Opening Polymerization.

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

Amplification-Free Detection of Highly Structured RNA Molecules Using SCas12aV2.

Bio-protocol·2026
Same author

Diagnostic accuracy of dual-phase cone-beam computed tomography for celiac arteriography in patients with hepatocellular carcinoma: Comparison with preoperative dynamic contrast-enhanced magnetic resonance imaging.

Journal of cancer research and therapeutics·2026
Same author

USP5 in cancer: a therapeutic window into metabolism and drug resistance.

Journal of translational medicine·2026

Related Experiment Video

Updated: Jun 4, 2026

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
05:48

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

Stereoselective Ring-Opening Polymerization of Racemic Dithiolactones Assisted by Non-Classical C─H⋯X Interactions.

Yanchao Wang1, Chenyang Guo1, Xue Wang1

  • 1State Key Laboratory of Polymer Science and Technology, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, P.R. China.

Angewandte Chemie (International Ed. in English)
|June 3, 2026
PubMed
Summary

This study introduces a novel catalytic system for ultrafast, stereoselective polymerization of recyclable dithiolactones. The method yields high-performance, stereoregular polythioesters with enhanced thermal properties and mechanical strength.

Keywords:
chemically recyclablenon‐classical hydrogen bondingpolythioestersring‐opening polymerizationstereoselective polymerization

More Related Videos

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

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 4, 2026

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
05:48

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

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
  • Catalysis
  • Materials Science

Background:

  • Stereoselective polymerization is crucial for high-performance recyclable polymers.
  • Achieving rapid, controlled, and stereoselective chain growth in polymerization remains a significant challenge.

Purpose of the Study:

  • To develop a catalytic system for highly stereoselective ring-opening polymerization.
  • To synthesize stereoregular, chemically recyclable polythioesters with enhanced properties.

Main Methods:

  • Utilized a catalytic system based on non-classical C─H⋯X hydrogen-bonding interactions.
  • Employed a bulky quaternary ammonium cation to create a confined environment for monomer and chain end orientation.
  • Performed ultrafast and stereoselective ring-opening polymerization of rac-dithiolactones in dichloromethane (DCM).

Main Results:

  • Achieved highly stereoselective ring opening, yielding stereoregular polythioesters (Pm up to 0.97, Mn up to 225.6 kDa).
  • The synthesized polythioesters are fully recyclable and form stereocomplexes, boosting the melting temperature (Tm) from 120.1°C to 224.1°C.
  • The polymers exhibit polyolefin-like mechanical performance.

Conclusions:

  • Non-classical hydrogen-bonding interactions play a key role in stereocontrol during polymerization.
  • The developed catalytic system provides a robust route to stereoregular, chemically recyclable polythioesters with superior thermal and mechanical properties.