N–Ethylbenzylammonium Fluorochromate (VI) Adsorbed on Silica Gel, a Mild and Selective Heterogeneous Reagent

S. Zahra Sayyed–Alangi* and Mohammad T. Baei

Islamic Azad University, Azadshahr Branch, Department of Chemistry, Azadshahr, Golestan, Iran. Tel. (+98)1722240194, Fax. (+98)1746724003. zalangi_szalangi@yahoo.com

Received July 12, 2010.
Accepted September 8, 2010.

Abstract

A mild and selective method for the oxidation of primary and secondary alcohols to their corresponding aldehydes and ketones with N–ethylbenzylammonium fluorochromate (VI), EBAFC, is reported. Stability, reaction rate, ease of work–up and efficiency of the EBAFC are considerably increased upon its adsorption on silica gel. The N–emylbenzylammonium fluorochromate (VI) adsorbed on silica gel is inert to aldehydes, ketones, oximes, thiols, sulfides, phenols, pyrans, trimethylsilanes, malonates and thioacetamides.

Keywords: N–ethylbenzylammonium Fluorochromate (VI), Heterogeneous Oxidant, Alcohols, Aldehyde, Ketone.

Resumen

Se describe un método suave y selectivo para la oxidación de alcoholes primarios y secundarios a sus aldehidos y cetonas correspondientes, con el fluorocromato de N–etil bencil amonio (FCEBA). La estabilidad, la velocidad de la reacción, la facilidad en el trabajo de la reacción y la eficiencia del FCEBA se incrementan considerablemente cuando este reactivo se adsorbe sobre gel de sílice. El fluorocromato de N–etil bencil amonio (VI) adsorbido sobre gel de sílice es inerte con aldehidos, cetonas, oximas, tioles, sulfuros, fenoles, piranos, trimetilsilanos, malonatos y tioacetamidas.

Palabras clave: Fluorocromato de N–etil bencil amonio (VI), Oxidantes heterogéneos, Alcoholes, Aldehídos, Cetonas.

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