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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...

Cycloaddition Reactions: Overview

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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.

Olefin Metathesis Polymerization: Overview

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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.
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Related Experiment Video

Updated: Jul 3, 2026

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

Controlled cyclopolymerization through quantitative 19-membered ring formation.

Bungo Ochiai¹, Yuuko Ootani, Takeshi Endo

¹Department of Polymer Science and Engineering, Faculty of Engineering, Yamagata University, Jonan 4-3-16, Yonezawa, Yamagata, Japan.

Journal of the American Chemical Society

|July 26, 2008

Summary

This study details the cyclopolymerization of a novel bis-methacrylate monomer, forming a large 19-membered ring. Controlled polymerization techniques were employed to achieve quantitative cyclization, highlighting the role of steric and hydrogen bonding effects.

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Published on: June 20, 2019

Area of Science:

Polymer Chemistry
Organic Synthesis
Macromolecular Science

Background:

Cyclopolymerization offers a route to novel cyclic polymers.
Controlling ring size in polymerization is challenging.
Bis-methacrylate monomers can undergo cyclization reactions.

Purpose of the Study:

To investigate the cyclopolymerization of a specific bis-methacrylate monomer.
To understand the factors influencing large ring formation.
To achieve controlled polymerization and quantitative cyclization.

Main Methods:

Synthesis of a bis-methacrylate monomer from trans-cyclohexanediol and 2-methacryloyloxyethyl isocyanate.
Cyclopolymerization reaction.
Reversible Addition-Fragmentation chain Transfer (RAFT) polymerization using cumyl dithiobenzoate.

Main Results:

The cyclopolymerization successfully formed 19-membered rings.
Steric effects from the cyclohexane ring and hydrogen bonding influenced ring size.
RAFT polymerization demonstrated controlled polymerization kinetics.
Quantitative cyclization was achieved, supporting the controlled polymerization.

Conclusions:

Designed steric regulation and hydrogen bonding can promote the formation of unusually large rings in cyclopolymerization.
RAFT polymerization is effective for controlled cyclopolymerization of this monomer.
The study provides insights into the synthesis of macrocyclic polymers.