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Pinnick oxidation : ウィキペディア英語版
Pinnick oxidation
The Pinnick oxidation is an organic reaction by which aldehydes can be oxidized into their corresponding carboxylic acids using sodium chlorite (NaClO2) under mild acidic conditions. It was originally developed by Lindgren and Nilsson. The typical reaction conditions used today were developed by G. A. Kraus, and H.W. Pinnick later proved that these conditions were generally applicable to a wide variety of systems. There exist many different reactions to oxidize aldehydes, but only a few are amenable to a broad range of functional groups. The Pinnick oxidation has proven to be both tolerant of sensitive functionalities and capable of reacting with sterically hindered groups. This reaction is especially useful for oxidizing α,β-unsaturated aldehydes, and another one of its advantages is its relatively low cost.
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==Mechanism==
The proposed reaction mechanism involves chlorous acid as the active oxidant, which is formed under acidic conditions from chlorite.
:ClO2 + NaH2PO4 HClO2 + NaHPO4
First, the chlorous acid adds to the aldehyde. Then resulting structure undergoes a pericyclic fragmentation in which the aldehyde hydrogen is transferred to an oxygen on the chlorine, with the chlorine group released as hypochlorous acid (HOCl).
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