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Synlett 2011(10): 1477-1478  
DOI: 10.1055/s-0030-1260574
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© Georg Thieme Verlag Stuttgart ˙ New York

Phosphorus Oxychloride

Fabien Caillé*
Institut de Chimie Organique et Analytique (ICOA), UMR-CNRS 6005, Université d"Orléans, rue de Chartres, 45063 Orléans cedex 2, France , Centre de Biophysique Moléculaire (CBM), UPR 4301 ­CNRS, rue Charles Sadron, 45071 Orléans cedex 2, France
e-Mail: fabien.caille@univ-orleans.fr;
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Publication Date:
26 May 2011 (online)

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Introduction

Phosphorus oxychloride (POCl3) is a common and intensively used inorganic compound industrially prepared from phosphorus trichloride either by oxidation with oxygen or chlorination followed by treatment with phosphorus pentoxide (Scheme  [¹] ). Despite it reacts violently with water, this stable colorless liquid has been extensively studied for decades to promote the synthesis of diverse heterocycles, [¹] such as the Bischler-Napieralski formation of isoquinolines [²] and its related cyclisations [³] , the Meth-Cohn approach to quinolines [4] or the Robinson-Gabriel route to oxazole. [5] Beyond the heterocyclic chemistry, phosphorus oxychloride is a powerful reagent for various functionalization like chlorinations, [6] Vilsmeier-Haack formylations [7] or dehydratations. [8] POCl3 also appears as a key reagent in bioorganic chemistry to phosphorylate proteins [9] or nucleosides, [¹0] and enters in the preparation of some polymers. [¹¹]

Scheme 1  Industrial preparation of phosphorus oxychloride

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