Permanganate, oxidizing reagent

Figure 10-32 shows one common reagent mixture (the Jones reagent — Cr03/H2S0yacetone). Another common procedure is a two-step reaction where basic potassium permanganate oxidizes the aldehyde to a carboxylate ion and the second step involves the acidification of the product to form the carboxylic acid. 

Ceric ammonium nitrate is used as a volumetric oxidizing reagent in many oxidation-reduction titrations. Cerium(IV) ion is a strong oxidant simdar to permanganate ion. It is the most widely-used primary standard among all Ce(IV) compounds. Other apphcations of this compound are in organic oxidation reactions and as a catalyst in polymerization of olefins. 

Alternative methods for removing 1-propenyl groups under non-acidic conditions have been reported these include reaction with alkaline potassium permanganate solution,204,205 ozonolysis followed by alkaline hydrolysis,204 205 treatment with a mercuric chloride-mercuric oxide reagent,206,207 and treatment with palladium on activated charcoal in a hydroxylic solvent containing a trace of an acid.2070 The last procedure is a combined isomerization-hydrolysis, but the isomerization step may be independently achieved by omission of the acid.2070,2076... 

Abraham, S. Rajan, P. K. Sreekumar, K. Poly(methyl methacrylate)-Sup-ported Pyrazolinium Permanganate A New Oxidizing Reagent, Polym. J. 1997, 29, 12. 

With oxidative reagents of a nucleophilic nature such as sodium and potassium permanganate, sulfoxides react faster than sulfides and a chemoselective oxidation of a sulfoxide in preference to that of a sulfide is available [77-79]. 

Several oxidizing reagents react with alkenes under mild conditions to give, as the overall result, addition of hydrogen peroxide as HO—OH. Of particular importance are alkaline permanganate (MnO40) and osmium tetroxide (0s04), both of which react in an initial step by a suprafacial cycloaddition mechanism like that postulated for ozone. 

The selective oxidation of alcohols is widely recognized as one of the most fundamental transformations in both laboratory and industrial synthetic chemistry because the resulting carbonyl compounds serve as important and versatile intermediates for the synthesis of fine chemicals [4]. Many oxidizing reagents, including permanganate and dichromate, have traditionally been employed to achieve this transformation [5]. These stoichiometric oxidants, however, have serious... 

Oxidation.1 Hydrated copper permanganate oxidizes alcohols in CH2C12 rapidly and in high yields. Ketones are obtained from secondary alcohols, and carboxylic acids from primary and benzylic alcohols. Primary or secondary allylic alcohols are also oxidized efficiently. Anhydrous reagent is much less active. 

Oxidizing reagents such as tetravalent cerium or potassium permanganate solutions may be standardized by oxalic acid, sodium oxalate, or potassium iodide. The reactions of Ce4+ and permanganate ions with oxalic acid in acid medium are given below ... 

The oxidation of alkenes by permanganate is one of the frequently used examples in freshman chemistry. It is also well known as the Baeyer test for unsaturation. There are many reagents that add two hydroxyl groups to a double bond,44 but osmium tetroxide and permanganate are the most prominent ones. The mechanism of the permanganate oxidation is believed to be similar to the oxidation of alkenes by 0s0445 46... 

OXIDATION, REAGENTS Barium mangan-ate. Benzyl(triethyl)ammonium permanganate. Bispyridinesilver permanganate. Bis(trimethylsilyl)peroxide. t-Butyl hydroperoxide. t-Butyl hydroperoxide-Benzyltri-methylammonium tetrabromooxomolyb-dale. t-Butyl hydroperoxide-Bisoxobis-(2,4-pentadionato)molybdenum. t-Butyl hydroperoxide-Chromium carbonyl. t-Bu-tyl hydroperoxide-Dialkyl tartrate-Titan-ium(IV) isopropoxide. t-Butyl hydroper-... 

Azaindoles are more stable to air oxidation than indoles, are stable to mild reagents like silver oxide and selenium dioxide, but are readily attacked by permanganate. In the structure proof of 7-aza-indole, Kruber oxidized the 1-benzenesulfonyl derivative with potassium permanganate in acetone solution to obtain 2-(benzene-sulfonyl)aminonicotinic acid. The 1-acetyl and 1-benzoyl derivatives gave inconsistent results, which Kruber attributed to their ease of hydrolysis. l-Benzoyl-2,5-dimethyl-4-azaindole and its 3-substituted derivatives give 3-benzamido-6-methylpicolinic acid with permanganate oxidation. ... 

Several oxidizing reagents other than ozone also cause doublo-bond cleavage. For example, potassium permanganate fKMrtO ) in neutral or acidic solution cleaves alkenes, giving carbonyl-containing products in low... 

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