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.[1] The typical reaction conditions used today were developed by G. A. Kraus.[2][3] H.W. Pinnick later demonstrated that these conditions could be applied to oxidize α,β-unsaturated aldehydes.[4] 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.[4][5]
PinnickOxidationReaction
^Lindgren, Bengt O.; Nilsson, Torsten; Husebye, Steinar; Mikalsen, ØYvind; Leander, Kurt; Swahn, Carl-Gunnar (1973). "Preparation of Carboxylic Acids from Aldehydes (Including Hydroxylated Benzaldehydes) by Oxidation with Chlorite". Acta Chem. Scand.27: 888–890. doi:10.3891/acta.chem.scand.27-0888.
^George A. Kraus; Bruce Roth (1980). "Synthetic studies toward verrucarol. 2. Synthesis of the AB ring system". J. Org. Chem.45 (24): 4825–4830. doi:10.1021/jo01312a004.
^George A. Kraus; Michael J. Taschner (1980). "Model studies for the synthesis of quassinoids. 1. Construction of the BCE ring system". J. Org. Chem.45 (6): 1175–1176. doi:10.1021/jo01294a058.
^ abBal, B. S.; Childers, W.E.; Pinnick, H.W. (1981). "Oxidation of α,β-Unsaturated Aldehydes". Tetrahedron. 37 (11): 2091–2096. doi:10.1016/S0040-4020(01)97963-3.
^Mundy, B. J.; Ellerd, Michael G.; Favaloro, Frank G. (2005). "Pinnick Oxidation". Name Reactions and Reagents in Organic Synthesis. John Wiley & Sons. p. 518. ISBN 978-0-471-22854-7.
The Pinnickoxidation is an organic reaction by which aldehydes can be oxidized into their corresponding carboxylic acids using sodium chlorite (NaClO2)...
Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters...
mnemonic. Some reactions such as the Pummerer rearrangement, the Pinnickoxidation and the Birch reduction are named for people other than their discoverers...
is used as hypochlorite scavenger in the oxidation of aldehydes with chlorite such as the Pinnickoxidation. Upon heating sulfamic acid will react with...
oxidation of an aliphatic and an α,β-unsaturated aldehyde. Later hydrogen peroxide also proved to work to remove the hypochlorite. Pinnickoxidation Lindgren...
the resulting alcohol. Ozonolysis of the silyl ether and Lindgren–Pinnickoxidation of the aldehyde afforded the keto acid. Ketone 2 was constructed via...
oxidation. (12) Epoxidation is usually more facile than C-H oxidation, although sterically hindered allyl groups may undergo selective C-H oxidation instead...
subsequently be used as substrates in the Rubottom oxidation. Below are some representative Rubottom oxidation products synthesized in the seminal papers. In...
Reaction". Chemical Reviews. 55 (1): 137–155. doi:10.1021/cr50001a003. Pinnick, Harold W. (1990). "The Nef Reaction". In Paquette, Leo A. (ed.). Organic...
live with such notables as Ringo Starr, Stevie Wonder, Neil Young, Doug Pinnick, Ron Wood, Rihanna, Robbie Krieger, Bruce Springsteen, Joe Walsh, Dave...
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