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Un nuevo tipo de silileno N-heterocíclico con reactividad ambivalente

Matthias Driess¹, Shenglai Yao, Markus Brym

¹Institute of Chemistry: Metalorganics and Inorganic Materials, Technische Universität Berlin, Strasse des 17. Juni 135, Sekr. C2, D-10623 Berlin, Germany. matthias.driess@tu-berlin.de

Journal of the American Chemical Society

|July 27, 2006

Resumen

Los investigadores sintetizaron un nuevo compuesto de silicio, un silileno, que muestra una reactividad única con los electrófilos. Esta reactividad, distinta de su contraparte de germanio, se atribuye al silileno.

Área de la Ciencia:

Química del organosilicio Química del organosilicio
Grupo Principal Elementos de la Química de los Elementos
Intermedios reactivos y reactivos.

Sus antecedentes:

Los compuestos divalentes del silicio (sililenos) son intermediarios reactivos.
Comprender su reactividad es crucial para las aplicaciones sintéticas.
La comparación con compuestos de germanio relacionados puede dilucidar los efectos electrónicos.

Objetivo del estudio:

Para informar sobre la síntesis de un nuevo compuesto de silicio divalente.
Para investigar su reactividad con los electrófilos.
Para comparar su reactividad con congéneres de germanio y explicar las diferencias.

Principales métodos:

Síntesis a través de la desbrominación de un precursor del dibromosililo.
Estudios de reactividad con varios electrófilos (R-X).
Cálculos de la Teoría Funcional de la Densidad (DFT).

Principales resultados:

Se sintetizó con éxito un nuevo silileno.
El silileno exhibió una reactividad única hacia los electrófilos (R-X).
Los cálculos de DFT indicaron una mayor basicidad de los pares de electrones solitarios de silileno en comparación con el germileno.
La adición de Me3SiX al sileno produjo un 1,4-adduct, que se reorganizó a un 1,1-adduct.

Conclusiones:

El silileno sintetizado muestra distintos patrones de reactividad.
La mayor basicidad electrónica del silileno explica sus reacciones electrófilas únicas.
La formación y reordenación de adutos observados proporcionan información sobre los mecanismos de reacción del silileno.

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