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Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

Oxidations of Aldehydes and Ketones to Carboxylic Acids

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Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic...
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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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...
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Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation01:22

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Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is...
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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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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Oxidación tipo Wacker controlada por catalizador: fácil acceso a aldehídos funcionalizados.

Zachary K Wickens1, Kacper Skakuj, Bill Morandi

  • 1Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.

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Resumen
Este resumen es generado por máquina.

Una nueva oxidación de Wacker modificada por nitrito convierte eficientemente alquenos oxigenados en aldehídos con alta selectividad. Este método facilita la síntesis enantioselectiva de productos farmacéuticos como la atomoxetina.

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Área de la Ciencia:

  • Química orgánica es la química orgánica.
  • La catálisis de la catálisis.
  • Metodología sintética de la metodología sintética.

Sus antecedentes:

  • La oxidación de Wacker es una piedra angular de la funcionalización de los alquenos.
  • La oxidación selectiva de alquenos oxigenados sigue siendo un desafío sintético.
  • El desarrollo de nuevos sistemas catalíticos es crucial para una síntesis eficiente.

Objetivo del estudio:

  • Para desarrollar una oxidación selectiva de aldehídos de alquenos con grupos de oxígeno alilo/homoalilo.
  • Para lograr altos rendimientos y selectividad utilizando una oxidación modificada de Wacker.
  • Explorar la utilidad de este método en la síntesis de agentes farmacéuticos y comprender los aspectos mecánicos.

Principales métodos:

  • Oxidación de Wacker de alquenos oxigenados modificados por nitrito.
  • Utilizando materiales de partida fácilmente disponibles.
  • Síntesis enantioselectiva de la atomoxetina.
  • Investigación de la influencia del grupo funcional en la reacción anti-Markovnikov.

Principales resultados:

  • Se logra hasta un 88% de rendimiento de aldehído y un 97% de selectividad de aldehído.
  • Demostró la aplicabilidad del método en la síntesis de la atomoxetina farmacéutica.
  • Obtuvo conocimientos mecanicistas preliminares sobre la reacción anti-Markovnikov influenciada por grupos proximales.

Conclusiones:

  • La oxidación de Wacker modificada por nitrito proporciona una ruta eficiente a los aldehídos de los alquenos oxigenados.
  • Esta metodología permite la síntesis rápida y enantioselectiva de compuestos valiosos.
  • La comprensión de los efectos del grupo funcional ofrece vías para futuras optimizaciones de reacción y estudios mecanicistas.