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Generación mediada por luz visible de trans-arilociclohexenos y su utilización en la síntesis de éteres con puente

Jon I Day¹, Kamaljeet Singh¹, Winston Trinh¹

¹107 Physical Science, Department of Chemistry , Oklahoma State University , Stillwater , Oklahoma 74078 , United States.

Journal of the American Chemical Society

|July 13, 2018

Resumen

Los investigadores desarrollaron un método para utilizar el transciclohexeno inestable para la síntesis. Mediante el uso de enlaces de hidrógeno, superaron su corta vida útil, lo que permitió la creación de éteres oxabicíclicos únicos.

Área de la Ciencia:

Química orgánica
Química sintética

Sus antecedentes:

El transciclohexeno es altamente tenso y reactivo, pero difícil de sintetizar debido a su corta vida útil.
Las aplicaciones sintéticas anteriores del transciclohexeno estaban limitadas por su inestabilidad.

Objetivo del estudio:

Desarrollar condiciones sencillas para el acceso a los trans-arilociclohexenos.
Demostrar la utilidad de los trans-arilociclohexenos en la síntesis de éteres oxaciclicos.
Para superar la corta vida útil del transciclohexeno para aplicaciones sintéticas.

Principales métodos:

Irradiación UV del cisciclohexeno para generar el transciclohexeno.
Utilizando la preorganización a través de enlaces de hidrógeno entre el sustrato y el socio de reacción.
El uso de trans-arilociclohexenos en la formación de éteres oxaciclicos.

Principales resultados:

Síntesis exitosa de una clase de trans-arilociclohexenos.
Utilidad demostrada en la formación de éteres oxabicíclicos no accesibles desde el cis-ciclohexeno.
Enlace de hidrógeno establecido como una estrategia para estabilizar el transciclohexeno para la síntesis.

Conclusiones:

El método desarrollado proporciona acceso a valiosos trans-arilociclohexenos.
Los éteres oxabicíclicos pueden sintetizarse utilizando este nuevo enfoque.
La estabilización del transciclohexeno a través de la preorganización es una estrategia viable para la química sintética.

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