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synthesis and reactions of n-methylbenzylammonium fluorochromate(vi) on silica gel, a selective and efficient heterogeneous oxidant的合成和反应n-methylbenzylammonium fluorochromate硅胶(vi),选择性和高效的异构的氧化剂.pdf

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Molecules 2004, 9, 825-829 molecules ISSN 1420-3049 http// Synthesis and Reactions of N-Methylbenzylammonium Fluorochromate(VI) on Silica Gel, a Selective and Efficient Heterogeneous Oxidant M. Z. Kassaee *, S. Z. Sayyed-Alangi and H. Sajjadi-Ghotbabadi Department of Chemistry, Tarbiat Modarres University, P.O. Box 14155-4838, Tehran, Iran; Fax: (+98) 21-8006544 * To whom correspondence should be addressed; E-Mail: Kassaeem@Modares.ac.ir Received: 28 June 2003; in revised form: 11 June 2004 / Accepted: 15 June 2004 / Published: 30 September 2004 Abstract: N-Methylbenzylammonium fluorochromate(VI) (MBAFC) is easily synthesized by addition of N-methylbenzylamine to an aqueous solution of CrO3 and HF. MBAFC shows selectivity in the oxidation of aryl alcohols to their corresponding aldehydes and ketones under mild conditions. The durability, ease of work up and efficiency of MBAFC are considerably increased upon its absorption on silica gel. Keywords: N-Methylbenzylammonium fluorochromate(VI); heterogeneous oxidants; silica gel; oxidation; alcohols. Introduction Chromium(VI) based reagents are widely used in modern organic synthesis for the oxidation of a variety of compounds under anhydrous and aprotic conditions, including primary and secondary alcohols. Extensive work has led to the development of a good number of these oxidants such as the Collins reagent [1], chromium trioxide-3,5-dimethylpyrazole complex [2], pyridinium chloro- chromate (PCC) [3], pyridinium dichromate (PDC) [4], 2,2-bipyridinium chlorochromate (BIPCC) [5], pyridinium fluorochromat

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