Jove
Visualize
Contáctanos
JoVE
x logofacebook logolinkedin logoyoutube logo
ACERCA DE JoVE
Visión GeneralLiderazgoBlogCentro de Ayuda JoVE
AUTORES
Proceso de PublicaciónConsejo EditorialAlcance y PolíticasRevisión por ParesPreguntas FrecuentesEnviar
BIBLIOTECARIOS
TestimoniosSuscripcionesAccesoRecursosConsejo Asesor de BibliotecasPreguntas Frecuentes
INVESTIGACIÓN
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchivo
EDUCACIÓN
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualCentro de Recursos para ProfesoresSitio de Profesores
Términos y Condiciones de Uso
Política de Privacidad
Políticas

Videos de Conceptos Relacionados

Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
Radical Chain-Growth Polymerization: Overview01:10

Radical Chain-Growth Polymerization: Overview

Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
Radical Chain-Growth Polymerization: Mechanism01:09

Radical Chain-Growth Polymerization: Mechanism

The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this species into the...
Radical Reactivity: Concentration Effects01:20

Radical Reactivity: Concentration Effects

In a radical reaction, the concentration of starting materials governs the selectivity of a radical. For example, the reaction between an alkyl halide and an alkene, in the presence of tin hydride and AIBN, begins with the generation of a tin radical. The generated radical then abstracts halogen from the alkyl halide, producing an alkyl radical. This alkyl radical can either react with tin hydride, yielding an alkane, or add to an alkene, generating a nitrile-stabilized radical, eventually...

También podría leer

Artículos Relacionados

Artículos vinculados a este trabajo por autores compartidos, revista y gráfico de citas.

Ordenar por
Same author

The key role of an intramolecular non-classical hydrogen bond of vinylboron monomer for stereoselective polymerization.

Nature communications·2026
Same author

Special Issue on Polymer Chemistry Research in Kyoto Institute of Polymer Science.

Macromolecular rapid communications·2026
Same author

Cascade Radical Isomerization Polymerization to Engineer Polymer Backbones.

Journal of the American Chemical Society·2026
Same author

Copper-Based Reversible Deactivation Radical Polymerization of Isopropenyl Boronate and Depolymerization of the Bromine-Terminated Polymer.

Macromolecular rapid communications·2026
Same author

Dynamic Chain Exchange of Amphiphilic Alternating/Random Copolymer Micelles Promoted by Structural Uniformity and Flexibility.

Small (Weinheim an der Bergstrasse, Germany)·2026
Same author

Water-Assisted Microphase Separation of Sodium Acrylate Random Copolymers Bearing Crystalline Alkyl Groups.

Macromolecular rapid communications·2025

Video Experimental Relacionado

Updated: Jun 21, 2026

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

Adición selectiva de radicales con un haluro heterobifuncional diseñado: un estudio primario hacia la polimerización

Shohei Ida1, Takaya Terashima, Makoto Ouchi

  • 1Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.

Journal of the American Chemical Society
|July 17, 2009
PubMed
Resumen

La adición de radicales catalizados por rutenio incorpora selectivamente el ácido metacrílico (MAA) utilizando una plantilla de haluro. Este método controla con precisión la incorporación de MAA, evitando la oligomerización y permitiendo una posible polimerización de precisión.

Más Videos Relacionados

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Videos de Experimentos Relacionados

Last Updated: Jun 21, 2026

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Área de la Ciencia:

  • Química orgánica es la química orgánica.
  • La ciencia de los polímeros es la ciencia de los polímeros.
  • La catálisis de la catálisis.

Sus antecedentes:

  • Las reacciones de adición radical son fundamentales en la síntesis orgánica.
  • El control de la selectividad en las reacciones radicales, especialmente con monómeros funcionalizados como el ácido metacrílico (MAA), sigue siendo un desafío.
  • La síntesis asistida por plantillas ofrece un nuevo enfoque para mejorar la especificidad de la reacción.

Objetivo del estudio:

  • Desarrollar un método de adición de radicales catalizados por rutenio (II) altamente selectivo para el ácido metacrílico (MAA).
  • Para investigar el papel de un haluro de plantilla con un grupo de amina incorporado en la dirección de la reacción.
  • Para demostrar una mayor selectividad del sustrato y el control sobre la polimerización.

Principales métodos:

  • Reacción de adición de radicales catalizada por rutenio (II).
  • Utilizando una plantilla de haluro que contiene un grupo amino para el reconocimiento de sustratos.
  • Experimentos de adición de radicales competitivos que comparan el MAA y el metacrilato de metilo (MMA).

Principales resultados:

  • Se logró una adición radical altamente selectiva y cuantitativa de MAA utilizando el haluro de la plantilla.
  • Se ha demostrado la formación preferencial de un adducto 1:1 de la plantilla de MAA debido a la unión iónica específica.
  • Se observó una mejora de más de 10 veces en la selectividad del sustrato (MAA frente a MMA) con la plantilla en comparación con un haluro sin plantilla.
  • Se descartó la oligomerización inducida por aminas externas en presencia de la plantilla.

Conclusiones:

  • La interacción específica de la plantilla de aminas con el grupo carboxilo de MAA es clave para la selectividad observada.
  • La proximidad de la amina de la plantilla al sitio de adición radical facilita un control preciso.
  • Este enfoque muestra potencial para controlar las secuencias de unidades de repetición en la polimerización de precisión.