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Hidratación catalítica de los alquenos terminales a los alcoholes primarios por hidratación catalítica de los

C M Jensen, W C Trogler

Science (New York, N.Y.)

|September 5, 1986

Resumen

Este estudio introduce una hidratación catalítica eficiente de alquenos terminales a alcoholes primarios utilizando un complejo de platino. Este método ofrece una ruta sintética barata y conveniente para la producción de valiosos alcoholes industriales.

Área de la Ciencia:

La catálisis de la catálisis.
Síntesis orgánica La síntesis orgánica.
Química organometálica Química orgánica de los metales.

Sus antecedentes:

La hidratación catalítica directa de alquenos terminales a alcoholes primarios es una transformación deseable pero difícil.
Los alcoholes industrialmente útiles se pueden sintetizar a través de métodos convenientes y rentables.

Objetivo del estudio:

Desarrollar un sistema catalítico para la hidratación directa de alquenos terminales a alcoholes primarios.
Para investigar el mecanismo de la hidratación de alquenos catalizada por un complejo de platino.

Principales métodos:

Utilizado trans-PtHCl(PMe3) 2 como precursor catalizador en una mezcla de agua y 1-hexeno.
Empleado la catálisis de transferencia de fase con cloruro de bencilo trietilamonio.
Realizó experimentos de etiquetado de deuterio para dilucidar el mecanismo de reacción.

Principales resultados:

Hidratación selectiva del 1-hexeno a n-hexanol a 6,9 volúmenes de negocio por hora.
Hidratación del 1-dodeceno a n-dodecanol a 8,3 volúmenes de negocio por hora.
El etiquetado de deuterio confirmó la eliminación reductora del enlace C-H en el proceso de hidratación.

Conclusiones:

El sistema de catalizador basado en platino permite una hidratación eficiente y selectiva de los alquenos terminales.
El mecanismo de reacción implica el ataque de hidróxido sobre el alqueno coordinado y la eliminación reductora del enlace C-H.
La actividad del catalizador depende de la concentración de hidróxido y las tasas de sustitución de alquenos.

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