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

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...

C–C Bond Cleavage: Retro-Aldol Reaction

C–C Bond Cleavage: Retro-Aldol Reaction

The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.

Mass Spectrometry: Cycloalkene Fragmentation

Mass Spectrometry: Cycloalkene Fragmentation

The molecular ions of cycloalkenes undergo fragmentation via a retro-Diels–Alder reaction.

Base-Catalyzed Ring-Opening of Epoxides

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...

Thermal Electrocyclic Reactions: Stereochemistry

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.

Olefin Metathesis Polymerization: Overview

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...

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Updated: May 25, 2025

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

Molecular Ring Remodeling through C-C Bond Cleavage.

Zengrui Cheng¹, Zhibin Hu¹, Ning Jiao^1,2,3

¹State Key Laboratory of Natural and Biomimetic Drugs, Chemical Biology Center, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191, China.

Accounts of Chemical Research

|February 27, 2025

Summary

This study introduces novel C-C bond cleavage strategies for molecular skeletal editing, enabling efficient ring expansion and ring-opening reactions under mild conditions for synthesizing complex molecules.

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Area of Science:

Organic Chemistry
Synthetic Chemistry
Catalysis

Background:

Stable carbon-carbon (C-C) bonds are fundamental in organic chemistry.
Direct C-C bond cleavage offers innovative pathways for molecular skeleton modification.
Molecular skeletal editing is a rapidly developing field with applications in drug discovery and materials science.

Purpose of the Study:

To present advancements in molecular ring remodeling via C-C bond cleavage.
To showcase cascade activation and entropy-driven reconstruction strategies.
To enable efficient synthesis of pharmaceuticals, natural products, and materials.

Main Methods:

Development of novel ring expansion reactions for C-, N-, and O-unit insertion.
Utilizing transition metal catalysis and radical-mediated processes for ring-opening reactions.
Investigating the challenging arene ring-opening (ARO) reaction.

Main Results:

Successful synthesis of amides, amines, lactones, and nitrogen-containing heterocycles via ring expansion.
Efficient construction of difunctionalized frameworks through C-C single and double bond cleavage in rings.
Stereoselective synthesis of conjugated systems via ARO reactions.

Conclusions:

Developed mild and efficient strategies for molecular ring remodeling through C-C bond cleavage.
Identified key intermediates and elucidated mechanisms, including entropy-driven reconstruction.
Expanded the synthetic toolbox for late-stage modification and complex molecule synthesis.