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Silaciclobutanona estabilizada por el donante: un precursor del 1-silaceto a través de la reacción de retro- [2 +

Thibault Troadec¹, Morelia Lopez Reyes¹, Ricardo Rodriguez¹

¹Université de Toulouse , UPS, and CNRS, LHFA UMR 5069, F-31062 Toulouse, France.

Journal of the American Chemical Society

|February 27, 2016

Resumen

Los investigadores sintetizaron la silicaciclobutanona estabilizada por el donante a través de la reacción de silicaciclopropileno y benzaldehído. Este compuesto se somete a retro- [2 + 2]-cicloadición a temperatura ambiente, obteniendo un nuevo 1-silaketeno y cis-estilbeno estabilizado por NHC.

Área de la Ciencia:

Química del silicio orgánico
Reacciones de cicloadición

Sus antecedentes:

Las siciclopropilidenas estabilizadas por el donante son productos intermedios reactivos.
El benzaldehído sirve como un electrófilo carbonilo común en la síntesis orgánica.

Objetivo del estudio:

Síntesis y caracterización de la silaciclobutanona estabilizada por el donante.
Investigar la estabilidad térmica y la reactividad de la silaciclobutanona sintetizada.

Principales métodos:

Reacción del siciclopropilideno 1 con el benzaldehído.
La catálisis por ácido de Lewis.
Caracterización espectroscópica de los productos.

Principales resultados:

Síntesis exitosa de silicaciclobutanona estabilizada por el donante 2.
Observación de la retroadición [2 + 2]-ciclo de silaciclobutanona a temperatura ambiente 2.
Formación de 1-silaketeno 4 estabilizado por N-heterocíclico (NHC) y cis-estilbeno.

Conclusiones:

Las silaciclobutanonas estabilizadas por el donante pueden sintetizarse en condiciones suaves.
El silaciclobutanona sintetizado exhibe una labilidad térmica única.
Esta reacción proporciona una nueva ruta a los intermediarios de silaketeno estabilizados por NHC.

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