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Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

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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...
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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

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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...
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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
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Unlike carbon, water, and nitrogen, phosphorus is not present in the atmosphere as a gas. Instead, most phosphorus in the ecosystem exists as compounds, such as phosphate ions (PO43-), found in soil, water, sediment and rocks. Phosphorus is often a limiting nutrient (i.e., in short supply). Consequently, phosphorus is added to most agricultural fertilizers, which can cause environmental problems related to runoff in aquatic ecosystems.
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La reacción fosfa-bora-Wittig

Andryj M Borys1, Ella F Rice1, Gary S Nichol1

  • 1EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Road, Edinburgh EH9 3FJ, United Kingdom.

Journal of the American Chemical Society
|August 26, 2021
PubMed
Resumen
Este resumen es generado por máquina.

Una nueva reacción de fosfa-bora-Wittig permite la síntesis directa de fosfaleceno utilizando compuestos de carbonilo fácilmente disponibles. Este método es paralelo a la reacción clásica de Wittig, ofreciendo nuevas vías sintéticas en la química del organofosforo.

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Área de la Ciencia:

  • Química de los organofosforos
  • Química orgánica sintética
  • Química del grupo principal

Sus antecedentes:

  • La reacción clásica de Wittig es una piedra angular para sintetizar alquenos a partir de compuestos carbonílicos.
  • Los fosfalicenos, análogos de fósforo de los alquenos, son valiosos intermedios sintéticos, pero su preparación puede ser un desafío.
  • Los fosborenos transitorios representan una clase de especies reactivas con potencial en nuevas formaciones de enlaces.

Objetivo del estudio:

  • Desarrollar una nueva vía sintética para la preparación directa de fosfaquenos.
  • Explorar la reactividad de los fosborenos transitorios con los compuestos carbonílicos.
  • Investigar los paralelos mecánicos entre la nueva reacción de fosfato-bora-Wittig y la reacción clásica de Wittig.

Principales métodos:

  • Reacción del fosboreno transitorio (Mes*PB-NR2) con varios compuestos carbonílicos (aldehídos, cetonas, ésteres y amidas).
  • Aislamiento y caracterización de los productos intermedios 1,2,3-fosfaboroxetanos.
  • Ciclorreversión de productos intermedios promovida por el ácido térmico o de Lewis para obtener fosfaquenos.
  • Estudios experimentales y cálculos de la teoría funcional de la densidad (DFT) para dilucidar los mecanismos de reacción.

Principales resultados:

  • La reacción fosfa-bora-Wittig produce con éxito fosfaalquenes a partir de diversos sustratos carbonílicos.
  • Los fosfaborenos transitorios reaccionan con los compuestos carbonílicos para formar 1,2,3-fosfaboratoxetanos, análogos a los oxafosfetanos de Wittig.
  • La ciclo-reversión de estos intermedios proporciona una vía viable hacia los fosfaquenos.
  • Los estudios de DFT y los datos experimentales confirman similitudes mecánicas significativas con la reacción clásica de Wittig.

Conclusiones:

  • La reacción fosfa-bora-Wittig ofrece un método directo y versátil para la síntesis de fosfalicenos.
  • La reacción se lleva a cabo a través de intermediarios de 1,2,3-fosfaboroxetano, reflejando el mecanismo de Wittig.
  • Este trabajo amplía la utilidad sintética de los fosborenos y proporciona nuevos conocimientos sobre las reacciones de olefinación basadas en fósforo.