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Videos de Conceptos Relacionados

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character,  phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen...
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Aldehydes and Ketones to Alkenes: Wittig Reaction Overview01:19

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

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The Wittig reaction is the conversion of carbonyl compounds—aldehydes and ketones—to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.
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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
2.9K
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

5.6K
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
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SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

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This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
8.1K
Preparation of Alcohols via Substitution Reactions01:38

Preparation of Alcohols via Substitution Reactions

5.7K
Overview
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group.  The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2,  depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides,...
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Video Experimental Relacionado

Updated: May 15, 2025

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

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Síntesis estereogénica mediante sustituciones catalíticas continuas

Gao-Liang Zheng1, Yuchen Zhang2, Jing-Ming Zhang1,3

  • 1State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, China.

Journal of the American Chemical Society
|April 9, 2025
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio introduce un nuevo método catalítico para la creación de compuestos estereogénicos de fósforo. Este enfoque ofrece una ruta versátil hacia moléculas importantes como los análogos de ProTide y los fármacos candidatos.

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Área de la Ciencia:

  • Química orgánica
  • Química medicinal
  • Catálisis

Sus antecedentes:

  • Los centros estereogénicos en fósforo son cruciales en las moléculas bioactivas y los organocatalisadores.
  • Los métodos de síntesis actuales dependen en gran medida de la resolución o el control diastereo, que requieren sustratos prefuncionalizados.
  • Los métodos catalíticos para generar estos centros son escasos y carecen de aplicabilidad general.

Objetivo del estudio:

  • Desarrollar una estrategia catalítica ampliamente aplicable, modular y enantioselectiva para la síntesis de compuestos estereogénicos en fósforo.
  • Establecer un método que evite la necesidad de sustratos prefuncionalizados.
  • Para demostrar la utilidad del protocolo en la síntesis de moléculas complejas.

Principales métodos:

  • Estrategia de sustitución continua enantioselectiva diseñada mediante el uso de precursores simples de fósforo.
  • Sustituciones nucleofílicas secuenciales para controlar la configuración estereofílica del producto.
  • Aplicación del protocolo para la síntesis de análogos y moléculas de ProTide.

Principales resultados:

  • Se accedió a una amplia gama de esqueletos estereogénicos en fósforo, incluidos los alkoxilfosforamidatos, los fosfatos, los fosforotioatos y los fosfonamidatos.
  • La estereoconfiguración de los productos fue fácilmente controlada por la secuencia de sustitución nucleofílica.
  • Se lograron síntesis concisas de análogos de ProTide y moléculas de fármacos, lo que demuestra el valor práctico del método.

Conclusiones:

  • La estrategia modular desarrollada proporciona un método catalítico general y eficiente para acceder a diversos compuestos estereogénicos de fósforo.
  • La capacidad del protocolo para controlar la estereoquímica y su aplicación en la síntesis de moléculas valiosas resaltan su importancia.
  • Los estudios computacionales y experimentales revelaron el apilamiento π-π y el enlace de calcógeno como factores clave que impulsan la estereoselectividad observada.