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Synlett 2006(19): 3364-3365  
DOI: 10.1055/s-2006-951561
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© Georg Thieme Verlag Stuttgart · New York

Pyridinium Dichromate - A Mild Oxidizing Reagent in Synthetic Organic Chemistry

Alessandro Kappel Jordão*
Instituto de Química, Universidade Federal Fluminense, UFF, 24020-150 Niterói, Rio de Janeiro, Brazil
e-Mail: alessandkappel@ig.com.br;
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Publication History

Publication Date:
23 November 2006 (online)

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Introduction

Pyridinium dichromate (PDC) is a mild and selective ­oxidizing agent mainly used to oxidize primary [1] and ­secondary alcohols. [2] It has several other applications such as in the rearrangement of allylic hydroxyl groups, [3] in the preparation of heterocycles, [4] the production of metal-free dienones, [5] [6] the oxidation of carbon-boron bonds [7] as well as in the preparation of enones [8] and in multicomponent ­reactions. [9] This reagent was discovered by E. J. Corey and G. Schmidt in 1979. [10] It is stable in solvents like DMF, DMSO, acetonitrile; it is sparingly soluble in dichloro­methane, chloroform and acetone. PDC is commercially available and easily prepared by addition of pyridine to a cooled solution of CrO3 in water at -30 °C. The resulting solution is diluted with acetone at -20 °C forming orange crystals that are collected by filtration.