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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
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Compuestos de bromo hipervalente estable en el banco: estrategia y plataforma versátiles para los bromuros estable en
Kazunori Miyamoto1,2, Motomichi Saito2, Shunsuke Tsuji2
1Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Journal of the American Chemical Society
|June 14, 2021
Resumen
Los investigadores desarrollaron una nueva estrategia para sintetizar bromanos lambda-3 estables. Este avance permite la creación de varios compuestos de bromo (III) estables al aire y a la humedad para diversas aplicaciones.
Área de la Ciencia:
- Química orgánica sintética
- Química del yodo y el bromo hipervalentes
Sus antecedentes:
- Los bromanos lambda-3 son compuestos reactivos y inestables.
- Los métodos sintéticos existentes para los bromanos son limitados.
Objetivo del estudio:
- Desarrollar una nueva estrategia para la síntesis de bromanos lambda-3 estables al aire y a la humedad.
- Caracterizar la estructura y la estabilidad de estos nuevos derivados de bromo.
Principales métodos:
- Estrategia cíclica de 1,2-benzbromoxol-3-one (BBX) para la síntesis de bromo.
- Cristalografía de rayos X, RMN y espectroscopia de infrarrojos para elucidación estructural.
Principales resultados:
- Síntesis exitosa de los bromanos lambda-3 estables al aire y a la humedad (9 y 10).
- Se ha demostrado la estabilización del centro de bromo (III) a través de la unión hipervalente intramolecular R-Br-O en N-triflilimino-lambda-3-bromano (12).
- Se generan diversos derivados estables que incluyen Br-hidroxi, -acetoxi, -alquinyl, -aryl y bis[(trifluorometil) sulfonil]metil bromano lambda-3.
Conclusiones:
- La estrategia BBX proporciona un método robusto para acceder a los bromanos lambda-3 estables.
- La unión hipervalente intramolecular es clave para la estabilidad observada.
- Este trabajo amplía el alcance de los compuestos de bromo hipervalentes estables.
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