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Related Concept Videos

Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic rearrangements are...
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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.
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,...
[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.
Step-Growth Polymerization: Overview01:03

Step-Growth Polymerization: Overview

Step-growth or condensation polymerization is a stepwise reaction of bi or multifunctional monomers to form long-chain polymers. As all the monomers are reactive, most of the monomers are consumed at the early stages of the reaction to form small chains of reactive oligomers, which then combine to form long polymer chains in the late stages. Hence, the reaction has to proceed for a long time to achieve high molecular weight polymers.
Many natural and synthetic polymers are produced by...

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Two consecutive click reactions as a general route to functional cyclic polyesters.

You-Yong Yuan1, Jin-Zhi Du, Jun Wang

  • 1Hefei National Laboratory for Physical Sciences at the Microscale, University of Science and Technology of China, Hefei, Anhui 230026, People's Republic of China.

Chemical Communications (Cambridge, England)
|November 9, 2011
PubMed
Summary

A new method creates functional cyclic polyesters using two click reactions. This versatile technique allows for the synthesis of advanced materials like cationic and thermo-responsive cyclic polyphosphoesters.

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Cyclic polymers offer unique properties compared to their linear counterparts.
  • Developing efficient and versatile synthetic routes to functional cyclic polymers remains a challenge.

Purpose of the Study:

  • To establish a simple and universal method for synthesizing functional cyclic polyesters.
  • To demonstrate the applicability of the method for creating advanced functional cyclic polymers.

Main Methods:

  • Utilized a two-step sequential click chemistry approach.
  • Employed azide-alkyne cycloaddition for initial cyclization of linear precursors.
  • Applied thiol-ene coupling for post-cyclization functionalization.

Main Results:

  • Successfully synthesized functional cyclic polyesters via a universal route.
  • Demonstrated the creation of functional cationic and thermo-responsive cyclic polyphosphoesters.
  • Validated the efficiency and versatility of the combined click reaction strategy.

Conclusions:

  • The presented method provides a straightforward and adaptable pathway to diverse functional cyclic polyesters.
  • This approach enables the synthesis of advanced cyclic polymers with tailored properties for various applications.