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The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Se sintetizaron nuevos fosfalauminirenos con un anillo de aluminio-carbono-fosforo (AlCP) de tres miembros tensados. Estos compuestos se someten a reacciones de apertura y ampliación del anillo, formando nuevos heterociclos del grupo principal.

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Área de la Ciencia:

  • Química organometálica
  • Química del grupo principal
  • Química sintética

Sus antecedentes:

  • Los complejos de aluminio son productos intermedios reactivos.
  • Las fosfalicinas son bloques de construcción versátiles en síntesis.
  • Los anillos de tres miembros a menudo exhiben una reactividad única debido a la tensión.

Objetivo del estudio:

  • Para sintetizar nuevos fosfalamirenos que contienen un anillo de tres miembros de AlCP.
  • Investigar la reactividad y la aromaticidad de estos sistemas de AlCP tensados.
  • Explorar la formación de nuevos heterociclos del grupo principal.

Principales métodos:

  • [1 + 2] reacción de cicloadición entre un complejo de aluminio (I) y fosfaquinos.
  • Síntesis de compuestos cristalinos de fosfalauminireno.
  • Cálculos de la teoría funcional de la densidad (DFT) para conocimientos mecanicistas.
  • Reacciones con varios sustratos (alcoholes, isocyanuros, carbenos, calcógenos, carbonilos, nitriles) para estudiar la apertura y el agrandamiento del anillo.

Principales resultados:

  • Síntesis de los fosfalamirenos HC[(CMe) ((NDipp) ]2Al[C(R) P] (2 y 3).
  • Pruebas computacionales para la aromaticidad de 2π-electrones en el anillo AlCP.
  • Apertura del anillo del compuesto 3 tras la protonación para producir el fosfalqueno 4.
  • Facil ampliación del anillo del compuesto 3 con diversos reactivos (CyNC, BAC, Se, Ph2CO, PhCHCHCOPh, PhCN) para formar heterociclos del grupo principal sin precedentes 5-10.
  • Preservación del enlace insaturado CP en los heterociclos recién formados.

Conclusiones:

  • Los fosfalauminirenos con anillos de AlCP tensados son accesibles a través de la cicloadición [1 + 2].
  • El anillo de AlCP exhibe un carácter aromático y sufre diversas reacciones de apertura y ampliación del anillo.
  • Esta química proporciona acceso a nuevos heterociclos del grupo principal con enlaces CP intactos.