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The attack of a nucleophile at the β carbon of an α,β-unsaturated carbonyl compound is called conjugate addition. Conjugate addition reactions of active methylene compounds, such as β-diketones, β-keto esters, β-keto nitriles, and α-nitro ketones, are called Michael addition reactions.
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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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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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Olefin Metathesis Polymerization: Overview01:13

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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.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists...
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The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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Updated: Jun 23, 2025

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Polímero de adición-eliminación y apertura de anillos

Yong-Liang Su1, Wei Xiong1, Liang Yue2

  • 1School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.

Journal of the American Chemical Society
|June 21, 2024
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio introduce un nuevo sistema de tioenona cíclica para la polimerización de apertura de anillos controlada utilizando un mecanismo de adición-eliminación Michael reversible. Este avance permite la síntesis de polímeros sintonizables y de alta calidad con potencial para la recuperación de monómeros.

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Área de la Ciencia:

  • Química de los polímeros
  • Síntesis orgánica
  • Ciencias de los materiales

Sus antecedentes:

  • La polimerización por apertura de anillos (ROP) es un método versátil para la síntesis de polímeros.
  • El desarrollo de métodos ROP controlados con reversibilidad dinámica sigue siendo un desafío.
  • Las tioenonas cíclicas ofrecen potencial como monómeros, pero requieren estrategias de polimerización innovadoras.

Objetivo del estudio:

  • Desarrollar un nuevo sistema cíclico de tioenona para la polimerización de apertura de anillos controlada.
  • Incorporar un mecanismo reversible de adición y eliminación de Michael (MAE) en el ROP.
  • Investigar la síntesis de politioenonas con propiedades sintonizables y pesos moleculares controlados.

Principales métodos:

  • Síntesis de nuevos monómeros cíclicos de tioenona.
  • La polimerización por apertura de anillos (ROP) utiliza un mecanismo de adición y eliminación de Michael (MAE) reversible.
  • Caracterización de las propiedades del polímero, incluido el peso molecular, la dispersión, la transparencia óptica y la resistencia mecánica.
  • Cálculos de la teoría funcional de la densidad (DFT) para aclarar los mecanismos de polimerización.

Principales resultados:

  • Se han desarrollado con éxito monómeros cíclicos de tioenona que permiten una ROP controlada a través de MAE.
  • Se han logrado condiciones de polimerización suaves, funcionalidades sintonizables, pesos moleculares controlados (Mn) y dispersiones estrechas.
  • Politioenonas sintetizadas con una excelente transparencia óptica y buenas propiedades mecánicas.
  • Recuperación demostrada de monómeros a través de la despolimerización.
  • Los cálculos de DFT proporcionaron información sobre las diferencias de conformación y reactividad de los monómeros entre los sistemas de tipane (TP) y tiocano (TC).

Conclusiones:

  • Los mecanismos MAE son factibles para la polimerización de apertura de anillo controlada.
  • La estrategia desarrollada ofrece una nueva vía para la síntesis de politioenonas funcionales.
  • Los resultados proporcionan directrices para el diseño de futuros monómeros para ROP controlados.