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Videos de Conceptos Relacionados

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic rearrangements are...
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.

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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
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Ciclo de adición intermolecular [2π+2π] catalizada por el hierro.

Sarah K Russell1, Emil Lobkovsky, Paul J Chirik

  • 1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.

Journal of the American Chemical Society
|May 24, 2011
PubMed
Resumen

Los complejos de hierro bis ((imino) piridina catalizan la [2π + 2π] cicloadición de etileno y butadieno. Se aisló un intermediario de metallociclo de hierro, revelando conocimientos sobre el mecanismo catalítico y las vías de ciclometalización.

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Área de la Ciencia:

  • Química organometálica Química orgánica de los metales.
  • La catálisis es la catálisis.
  • Síntesis orgánica La síntesis orgánica.

Sus antecedentes:

  • Los ligandos de bis ((imino) piridina son andamios versátiles en la química de la coordinación.
  • Los complejos de hierro se estudian cada vez más como alternativas sostenibles a los catalizadores de metales preciosos.
  • La fijación de nitrógeno y la formación de enlaces C-C son desafíos clave en la catálisis.

Objetivo del estudio:

  • Para investigar la actividad catalítica de los compuestos de dinitrógeno de hierro bis(imino) piridina en reacciones de cicloadición.
  • Para dilucidar el mecanismo de la cicloadición intermolecular [2π + 2π] de etileno y butadieno.
  • Identificar y caracterizar los intermediarios clave en el ciclo catalítico.

Principales métodos:

  • Síntesis y caracterización de los complejos de dinitrógeno de hierro bis ((imino) piridina.
  • Pruebas catalíticas para la cicloadición de etileno y butadieno.
  • Reacciones estequiométricas para aislar y estudiar los intermediarios de reacción.
  • Estudios de etiquetado de deuterio para sondear las vías de reacción.

Principales resultados:

  • Los complejos de hierro ((iPr) PDI) Fe (((N2)2) y [(Me) PDI) Fe (((N2) ]2 ((μ2-N2) catalizan de manera eficiente el ciclo de adición [2π + 2π].
  • Se aisló un intermediario de metallociclo de hierro y se demostró que era catalíticamente activo.
  • Se observó la eliminación reductora de C-C inducida por dieno del metalócico.
  • El etiquetado con deuterio reveló la ciclometalización competitiva de los sustituyentes del ligando arilo.

Conclusiones:

  • Los complejos de hierro bis ((imino) piridina son catalizadores efectivos para la síntesis de vinilciclobutano.
  • El ciclo catalítico involucra a un intermediario del metallociclo del hierro sometido a una eliminación reductora.
  • La ciclometalización de ligandos es una vía competidora durante la catálisis.