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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.
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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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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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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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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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Dimerización no covalente después de la ciclización de Enediyne en Au

Dimas G de Oteyza1,2, Alejandro Pérez Paz3, Yen-Chia Chen4

  • 1Donostia International Physics Center , E-20018 San Sebastián, Spain.

Journal of the American Chemical Society
|August 5, 2016
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Resumen

En las superficies de oro, el 1,2-bis(2-feniletinil) benceno sufre ciclización térmica preferentemente a través de la vía C(1) -C(6), formando una olefina ciclica tensa. Este producto luego se autoensambla en dímeros no covalentes.

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Área de la Ciencia:

  • Química de las superficies
  • Síntesis orgánica
  • Química computacional

Sus antecedentes:

  • La ciclización de la enediina en solución implica las vías C(1) -C(6) (Bergman) y C(1) -C(5) que compiten entre sí.
  • La química superficial de los productos de ciclización de enediina estérilmente obstaculizados es en gran medida inexplorada.

Objetivo del estudio:

  • Para investigar la ciclización inducida térmicamente de 1,2-bis-fenil-etinile-benceno en una superficie de oro.
  • Para aclarar el mecanismo de reacción y el comportamiento de autoensamblaje del producto.
  • Comprender la influencia de la superficie Au{11} en la vía de ciclización.

Principales métodos:

  • Microscopía de túnel de barrido (STM) para la observación de la superficie.
  • Simulaciones por ordenador para el análisis teórico.
  • Cálculos de la teoría funcional de la densidad (DFT) para el mecanismo y las fuerzas motrices.

Principales resultados:

  • La vía de ciclización C(1) -C(5) está suprimida en Au(111).
  • La ciclización C(1) -C(6) produce una nueva olefina bicíclica de alta tensión.
  • El producto de olefinas bicíclicas se autoensambla en dímeros discretos no unidos covalentemente en la superficie Au{11}.

Conclusiones:

  • La superficie Au{11} dirige la ciclización del 1,2-bis{2}-feniletinil) benceno hacia la vía C{1}-C{6}.
  • Se forma una olefina bicíclica de tensión única y muestra autoensamblaje en dímeros.
  • Los cálculos de DFT proporcionan información sobre el mecanismo de reacción y las interacciones no covalentes que impulsan la formación de dímeros.