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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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.
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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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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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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.
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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Rearreglo diotrópico quimioselectivo basado en Pd: fluorociclado y reacción regioselectiva de Wacker de amidas

Chen-Xu Liu1, Qian Wang1, Jieping Zhu1

  • 1Laboratory of Synthesis and Natural Products (LSPN), Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL-SB-ISIC-LSPN), BCH5304, CH-1015 Lausanne, Switzerland.

Journal of the American Chemical Society
|October 25, 2024
PubMed
Resumen

Este estudio introduce una nueva reacción catalizada por el paladio para sintetizar heterociclos fluorados a partir de precursores simples. El proceso crea eficientemente tres nuevos enlaces químicos, lo que permite la formación de valiosas 5,6-dihidro-4H-1,3-oxazinas.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Química del fluor

Sus antecedentes:

  • Las reacciones de fluorociclado ofrecen rutas eficientes para los heterociclos fluorados.
  • Las reacciones catalizadas por paladio son herramientas versátiles en la síntesis orgánica.
  • Las reacciones dominó agilizan las vías sintéticas realizando múltiples transformaciones secuencialmente.

Objetivo del estudio:

  • Desarrollar un proceso de dominó oxidativo catalizado por Pd (II) sin precedentes para sintetizar heterociclos fluorados.
  • Establecer un método único para la conversión de amidas homoalílicas en cetonas homologadas.
  • Para lograr la oxidación regioselectiva de Wacker de los alquenos 1,1-disubstituidos.

Principales métodos:

  • Utilizando un proceso de dominó oxidativo catalizado por Pd (II) que incluye oxipaladación, Pd (II) oxidación, reordenamiento diotrópico y eliminación reductiva.
  • El uso de amidas homoalílicas como materiales de partida.
  • Aprovechando la fácil hidrólisis de éteres alquilo terciarios α-fluoro en condiciones ácidas.

Principales resultados:

  • Se han sintetizado con éxito 5,6-dihidro-4H-1,3-oxazinas a partir de amidas homoalílicas en un solo paso.
  • Creado tres nuevos enlaces químicos bajo condiciones operacionales simples.
  • Desarrolló una conversión de una sola olla de amidas homoalílicas a cetonas homologadas a través de la oxidación regioselectiva de Wacker.

Conclusiones:

  • El proceso de dominó catalizado por Pd (II) proporciona una ruta eficiente y novedosa para los heterociclos fluorados.
  • La subsiguiente transformación de un solo recipiente ofrece un raro ejemplo de oxidación regioselectiva de Wacker para alquenos 1,1-disubstituidos.
  • Esta metodología amplía la utilidad sintética de la fluorociclado y la catálisis del paladio.