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Síntesis, estructura y termólisis de un pentacoordinado 1,2-oxastibetano

Yosuke Uchiyama¹, Naokazu Kano, Takayuki Kawashima

¹Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

Journal of the American Chemical Society

|October 30, 2003

Resumen

El pentacoordinado 1,2-oxastibetano sintetizado se somete a termólisis. La adición de sales controla la estereoquímica y las proporciones de producto, dando oxiranos u olefinas.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
La estereoquímica es la estereoquímica.
Química orgánica sintética y orgánica.

Sus antecedentes:

Los compuestos organometálicos pentacoordinados ofrecen una reactividad única.
Los 1,2-oxastibetanos son una clase de compuestos heterocíclicos con aplicaciones potenciales.

Objetivo del estudio:

Para sintetizar y caracterizar el pentacoordenado isomérico 1,2-oxastibetanes.
Para investigar los resultados estereoquímicos de su termólisis.

Principales métodos:

Síntesis de 1,2-oxastibetanos a través de la reacción de los bromo(2-hidroxialquilo) estiboranos con el hidruro de sodio.
Caracterización mediante cristalografía de rayos X y espectroscopia de RMN.
Estudios de termólisis con y sin aditivos (sales).

Principales resultados:

Síntesis exitosa del pentacoordinado isomérico 1,2-oxastibetanes.
La termólisis produce oxiranos con retención o inversión de la configuración, y olefinas.
Los aditivos de la sal (LiBr, LiBPh4·3DME) dictan la estereoquímica y la distribución del producto.

Conclusiones:

Los pentacoordinados 1,2-oxastibetanos son objetivos sintéticos accesibles.
La termólisis proporciona una ruta a los oxiranos y olefinas definidos estereoquímicamente.
El control por medio de sales sobre las vías de termólisis ofrece versatilidad sintética.

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