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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 atom and...
3.6K
Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

3.2K
In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
3.2K
Aldehydes and Ketones to Alkenes: Wittig Reaction Overview01:19

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

7.9K
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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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

5.9K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
5.9K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

10.4K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
10.4K
Oxidation of Alcohols02:37

Oxidation of Alcohols

13.3K
In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Desoxigenación de óxidos de fosfina mediante catálisis redox PIII/PVO a través de reacciones isodémicas sucesivas

Jing Xue1, Yu-Shan Zhang1, Zhen Huan1

  • 1Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing 100084, China.

Journal of the American Chemical Society
|July 6, 2023
PubMed
Resumen

Este estudio introduce un nuevo método catalítico para la desoxigenación de los óxidos de fosfina, crucial para la química del fósforo sostenible. El nuevo enfoque utiliza un catalizador cíclico de organofosforo y un reductor terminal en condiciones suaves, evitando reactivos agresivos.

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Área de la Ciencia:

  • Química de los organofosforados
  • Catálisis
  • Química sostenible

Sus antecedentes:

  • La desoxigenación de los óxidos de fosfina es vital para la síntesis de ligandos y catalizadores de fósforo.
  • El fuerte enlace doble fósforo-oxígeno (PO) presenta un desafío significativo debido a su inercia termodinámica.
  • Los métodos existentes a menudo requieren condiciones duras, ácidos de Lewis / Brønsted o reactivos halogenados estequiométricos.

Objetivo del estudio:

  • Desarrollar una estrategia catalítica fácil y eficiente para la desoxigenación de los óxidos de fosfina.
  • Para superar los desafíos termodinámicos asociados con la reducción del enlace PO.
  • Establecer una alternativa sostenible y suave a los métodos actuales de reducción.

Principales métodos:

  • Se desarrolló una nueva estrategia catalítica que emplea secuencias redox PIII/PO.
  • Se utilizaron reacciones isodémicas sucesivas, donde la fuerza motriz termodinámica para romper un enlace PO se compensa formando otro.
  • Se empleó un catalizador cíclico de organofosforo y fenilsilano (PhSiH3) como reductor terminal.

Principales resultados:

  • El sistema catalítico demostró una desoxigenación fácil y eficiente de los óxidos de fosfina.
  • La reacción se produjo en condiciones suaves, evitando activadores estequiométricos.
  • Se observó un amplio alcance de sustrato y reactividades excelentes.
  • Las investigaciones preliminares revelaron una doble función sinérgica del catalizador.

Conclusiones:

  • Se ha establecido con éxito un nuevo método catalítico para la desoxigenación del óxido de fosfina.
  • Este enfoque ofrece una alternativa sostenible y eficiente para la química del fósforo.
  • El catalizador de organofosforo cíclico juega un papel sinérgico crucial en el proceso redox PIII/PO.