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Cicloadición intramolecular reversible de fosfalqueno a un anillo de areno

Liu Leo Liu¹, Jiliang Zhou¹, Levy L Cao¹

¹Department of Chemistry , University of Toronto , 80 St. George Street , Toronto , Ontario M5S 3H6 , Canada.

Journal of the American Chemical Society

|May 7, 2019

Resumen

Los investigadores informan de la primera cicloadición reversible de un grupo principal de especies con vínculos múltiplos con un anillo areno. Este estudio explora las reacciones de cicloadición de fosfalqueno y su potencial para sintetizar nuevos compuestos bicíclicos.

Área de la Ciencia:

Química de los organofosforados
Química del grupo principal
Síntesis orgánica

Sus antecedentes:

Los cationes de fosfeninio son precursores de los fosfalicenos reactivos.
Las reacciones de cicloadición son fundamentales en la síntesis orgánica.
El grupo principal de especies de enlaces múltiples ofrece una reactividad única.

Objetivo del estudio:

Investigar las reacciones de cicloadición de fosfalicenos derivados de cationes de fosfeninio.
Para explorar la reversibilidad de estas reacciones de cicloadición.
Examinar la reactividad de los compuestos de fosfina bicíclicos resultantes.

Principales métodos:

Desprotonación de los cationes de fosfeninio para generar fosfalicenos.
Reacciones de cicloadición con anillos aromáticos.
Reacciones de oxidación y alquilación de los productos de fosfina cíclica.
Análisis computacional de los mecanismos de reacción y sus implicaciones.

Principales resultados:

La formación de fosfaliceno y la subsiguiente cicloadición a un anillo aromático unido a N produjo un 2-fosfabiciclo[2.2.2]octa-5,7-dieno.
Se observó un equilibrio reversible entre el fosfaliceno y el producto de cicloadición para un análogo menos voluminoso.
Las especies de fosfina bicíclica se sometieron a oxidación y alquilación.
Los estudios computacionales proporcionaron información sobre los mecanismos de reacción.

Conclusiones:

Se logró la primera cicloadición reversible de un grupo principal de especies con enlaces múltiples con un anillo areno.
Los hallazgos amplían el alcance de la química de la cicloadición que involucra a los principales elementos del grupo.
El estudio pone de relieve la utilidad sintética de los fosfalicenos y las fosfinas cíclicas.

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