El olimpiceno es una molécula orgánica que fue concebida en marzo de 2010 por los científicos Graham Richards de la Universidad de Oxford y Antony Williams y fue sintetizada por primera vez por los investigadores Anish Mistry y David Fox, de la Universidad de Warwick. La molécula fue obtenida como una manera de celebrar los Juegos Olímpicos de Londres 2012.
Este compuesto está formado por cinco anillos, de los cuales cuatro son anillos de benceno, unidos de manera muy similar a los anillos olímpicos, por tal razón lleva dicho nombre.
Síntesis del olimpiceno
La obtención del olimpiceno inicia mediante la reacción de Wittig del carboxaldehído de pireno. Se inicia haciendo reaccionar trifenilfosfina con bromoacetato de etilo para obtener el iluro. Luego el iluro o sal de fosfino es tratado con una base débil, y así esta es capaz de reaccionar con el aldehído en tolueno.
Seguidamente, luego de la hidrogenación del compuesto carbonílico insaturado alfa,beta empleando hidrógeno y paladio en acetato de etilo, el éster se transformó en el cloruro de ácido usando hidróxido de potasio, ácido y luego cloruro de tionilo.
A través de una reacción de Friedel-Crafts con cloruro de aluminio en diclorometano se produjo una cetona. Posteriormente, se redujo esta cetona con hidruro de aluminio y litio y como resultado se obtuvo el alcohol 3,4-dihidro-5H-benzo[cd]pireno-5-ol, al cual fue tratado con un ácido en forma de resina de intercambio iónico para lograr el compuesto final.
FUENTE
- Quimicafacil.net. Julio 20, 2021. Olimpiceno. – https://quimicafacil.net/compuesto-de-la-semana/olimpiceno/
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