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Related Concept Videos

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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

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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...
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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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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.
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

2.1K
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...
2.1K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

2.3K
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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Updated: Jun 28, 2025

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Stereoregular poly(2-phenylthiirane) via cationic ring-opening polymerization.

Yu Xiao1, Tian-Jun Yue1, Xiao-Bing Lu1

  • 1State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, Dalian University of Technology, 2 Linggong Road, Dalian, Liaoning 116024, China. tjyue189@dlut.edu.cn.

Chemical Communications (Cambridge, England)
|April 17, 2024
PubMed
Summary
This summary is machine-generated.

Researchers developed a new method for synthesizing polythioethers using cationic polymerization. This technique precisely controls the structure of poly(2-phenylthiirane) with high stereoregularity.

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis

Background:

  • Polythioethers are versatile polymers with diverse applications.
  • Controlled synthesis of polythioethers with specific structures remains a challenge.

Purpose of the Study:

  • To develop an effective strategy for synthesizing well-defined polythioethers.
  • To precisely control the regio- and stereochemistry during polymerization.

Main Methods:

  • Cationic polymerization of thiiranes with electron-withdrawing substituents.
  • Ring-opening polymerization of 2-phenylthiirane.

Main Results:

  • Achieved effective synthesis of polythioethers with a well-defined structure.
  • Demonstrated precise control over regio- and stereochemistry.
  • Produced poly(2-phenylthiirane) with high stereoregularity using enantiomerically pure thiirane.

Conclusions:

  • The described cationic polymerization strategy is effective for controlled polythioether synthesis.
  • This method enables the production of stereoregular poly(2-phenylthiirane).