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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

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Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone. 
When dissolved in liquid ammonia, an alkali metal, such as sodium,...
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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Reacciones catalíticas de transferencia de vinilideno reductor

Sudipta Pal1, You-Yun Zhou1, Christopher Uyeda1

  • 1Department of Chemistry, Purdue University , West Lafayette, Indiana 47907, United States.

Journal of the American Chemical Society
|August 16, 2017
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Resumen

Los investigadores desarrollaron una nueva reacción de metilenociclopropanación reductora catalítica utilizando olefinas simples y 1,1-dicloroalquenos. Este método sintetiza de manera eficiente los metilenociclopropanos estirados, valiosos intermedios sintéticos.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Metodología sintética

Sus antecedentes:

  • Los metilenociclopropanos son compuestos cíclicos de alta tensión con una utilidad sintética significativa.
  • Su síntesis a menudo requiere reactivos o condiciones especializadas.
  • La energía de deformación inherente de los metilenociclopropanos es superior a la de los ciclopropanos saturados.

Objetivo del estudio:

  • Desarrollar un nuevo método catalítico para la síntesis de metilenociclopropanos.
  • Utilización de 1,1-dicloroalquenos fácilmente disponibles como precursores para las unidades de vinilideno.
  • Para explorar el mecanismo de la metilenociclopropanación reductora catalítica.

Principales métodos:

  • El uso de un catalizador de níquel (Ni) dinuclear para promover la reacción.
  • Utilizando olefinas simples y 1,1-dicloroalquenos como materiales de partida.
  • Investigación de la formación propuesta de productos intermedios de Ni2 (vinilidenoides) mediante adición oxidativa de C-Cl.

Principales resultados:

  • Se logró una metilenciclopropanación reductora catalítica exitosa de las olefinas simples.
  • La reacción proporciona un acceso eficiente a las estructuras de metilenociclopropano.
  • El catalizador de Ni dinuclear facilita la transformación a través de los intermedios propuestos.

Conclusiones:

  • Se ha establecido una nueva vía sintética para los metilenociclopropanos.
  • El sistema catalítico ofrece un método eficiente para generar valiosos intermedios sintéticos.
  • El mecanismo propuesto que involucra a los intermediarios de Ni2 (vinylidenoid) proporciona una visión de la vía de reacción.