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

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Organic Chemistry

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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)
 
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21.25: 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 strain drives the reaction forward.

The characteristic feature of the ROMP is that the unsaturation present in the reactants is conserved in the products. The reactivity of cycloalkenes towards ROMP decreases with an increase in the ring size.

Poly(phenylene vinylene) (PPV), an important polymer having alternating phenyl and vinyl groups used for electro-optical applications, is prepared by ROMP reaction. Acetyl-substituted bicyclooctadiene undergoes ROMP in the presence of Grubbs catalyst and gives processable polymer which upon heating loses two moles of acetic acid and aromatizes to form poly(phenylene vinylene) polymer.

Figure1

Figure 1. ROMP synthesis of poly(phenylene vinylene).

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Keywords: Olefin Metathesis Polymerization Ring-opening Metathesis Polymerization ROMP Grubbs Catalyst Metallacyclobutane Unsaturated Open-chain Polymer Poly(phenylene Vinylene) PPV Electro-optical Applications Bicyclooctadiene Aromatization

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