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Videos de Conceptos Relacionados

Directing Effect of Substituents: meta-Directing Groups01:09

Directing Effect of Substituents: meta-Directing Groups

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Substituents on the benzene ring that direct an incoming electrophile to undergo substitution at the meta position are called meta directors. All meta directors either have a positive charge on the atom directly bonded to the ring or a partial positive charge. These groups function by withdrawing electrons from the ring through inductive and resonance effects. Consider the carbocation intermediates formed upon the addition of an electrophile on nitrobenzene at the...
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meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

4.6K
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
4.6K
Preparation of Nitriles01:12

Preparation of Nitriles

1.9K
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
1.9K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

5.0K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
5.0K
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

8.1K
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
8.1K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

3.0K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
3.0K

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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

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Funcionalización meta-selectiva de C-H utilizando un grupo de dirección a base de nitrilo y un éter Si-cleable.

Sunggi Lee1, Hyelee Lee, Kian L Tan

  • 1Boston College , 2609 Beacon Street Chestnut Hill, Massachusetts 02467.

Journal of the American Chemical Society
|December 12, 2013
PubMed
Resumen

Los investigadores desarrollaron una nueva plantilla basada en nitrilo para la funcionalización meta-selectiva de enlaces C-H. Este método versátil es práctico para varios ámbitos y grupos funcionales, simplificando la síntesis.

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Área de la Ciencia:

  • Química orgánica es la química orgánica.
  • Química sintética de la química sintética.

Sus antecedentes:

  • La funcionalización dirigida C-H es una poderosa herramienta sintética.
  • La funcionalización meta-selectiva de las arenas sigue siendo un desafío.
  • Los métodos existentes a menudo carecen de un amplio alcance de sustrato o tolerancia de grupo funcional.

Objetivo del estudio:

  • Desarrollar un nuevo grupo directivo basado en nitrilo para la funcionalización meta-selectiva de C-H.
  • Para demostrar la amplia aplicabilidad y tolerancia de grupo funcional de la plantilla desarrollada.
  • Crear un método sintéticamente práctico para la introducción y eliminación del grupo directivo.

Principales métodos:

  • Síntesis de un grupo de dirección a base de nitrilo con fijación de silicio.
  • Aplicación de la plantilla en reacciones meta-selectivas de funcionalización C-H.
  • Evaluación del alcance del sustrato con varias arenas sustituidas.
  • Evaluación de la tolerancia del grupo funcional bajo condiciones de reacción.

Principales resultados:

  • Se desarrolló con éxito una nueva plantilla basada en nitrilo que permite la funcionalización meta-selectiva de C-H.
  • La plantilla demostró su aplicabilidad a una amplia gama de arenas sustituidas.
  • El método mostró tolerancia a diversos grupos funcionales, mejorando su utilidad.
  • Se estableció una estrategia de fácil introducción y desprotección utilizando un enlace de silicio.

Conclusiones:

  • La plantilla basada en nitrilo desarrollada ofrece un enfoque práctico y versátil para la funcionalización meta-selectiva de C-H.
  • Esta metodología amplía el conjunto de herramientas sintéticas para modificar compuestos aromáticos.
  • La estrategia mediada por el silicio mejora la eficiencia general y la aplicabilidad en la síntesis orgánica.