Potassium permanganate, acetylene

Peroxides, organic Phosphorus (white) Potassium chlorate Potassium perchlorate Potassium permanganate Silver Acids (organic or mineral), avoid friction, store cold Air, oxygen Acids (see also chlorates) Acids (see also perchloric acid) Glycerol, ethylene glycol, benzaldehyde, sulphuric acid Acetylene, oxalic acid, tartaric acid, fulminic acid (produced in ethanol — nitric acid mixtures), ammonium compounds... 

N-Substituted amides derived from 2-chloro- or4-chloronicotinic acid react with CH-acidic nitriles in the presence of base to yield amino derivatives of [l,6]naphthytid-5(6//)-ones and [2,7]naphthyrid-l(2//)-ones <1997JHC397>. 3-(l-Alkylamino)pyridines react with electron-deficient alkynes (acetylene dicatboxylates) in the presence of acid to give l,2-dihydro[2,7]naphthyridine-3,4-dicarboxylates in up to 72% yield compounds unsubstituted at C-1 were readily oxidized with potassium permanganate to naphthyridine-l-ones <2005TL3953>. 

Tris(dimethylamino)sulfonium difluo-rotrimethylsilicate, 336 Xenon(II) fluoride, 345 Alkyl bromides Potassium permanganate, 258 Sodium bromide, 46 Tetraethylammonium bromide, 46 Alkyl iodides Aluminum iodide, 17 Potassium permanganate, 258 Sodium iodide, 46 Tetraethylammonium iodide, 46 Alkynes (see also Acetylenic carbonyl compounds, Diynes, Enynes, Propar-gyl alcohols)... 

In the course of investigations on allylic and acetylene-allene rearrangements of 3-substituted quinuclidines, it was found that by oxidation and ozonolysis of compounds with functional groups at positions allylic to the double bond, not only the double bonds but also the adjacent carbon-carbon bonds are broken. For example, in the oxidation of 3-hydroxy-3-vinylquinuclidine (119), with potassium permanganate under mild conditions, and in its ozonolysis, qui-nuclidin-3-one (2) is formed along with 3-hydroxy quinuclidine-3-carboxylic acid.161 The positions of double bonds in such systems can be firmly established by NMR spectroscopy, but not by oxidative methods.101... 

The spectrum of applications of potassium permanganate is very broad. This reagent is used for dehydrogenative coupling [570], hydrox-ylates tertiary carbons to form hydroxy compounds [550,831], hydroxylates double bonds to form vicinal diols [707, 296, 555, 577], oxidizes alkenes to a-diketones [560, 567], cleaves double bonds to form carbonyl compounds [840, 842, 552] or carboxylic acids [765, 841, 843, 845, 852, 869, 872, 873, 874], and converts acetylenes into dicarbonyl compounds [848, 856, 864] or carboxylic acids [843, 864], Aromatic rings are degraded to carboxylic acids [575, 576], and side chains in aromatic compounds are oxidized to ketones [566, 577] or carboxylic acids [503, 878, 879, 880, 881, 882, 555]. Primary alcohols [884] and aldehydes [749, 868, 555] are converted into carboxylic acids, secondary alcohols into ketones [749, 839, 844, 863, 865, 886, 887], ketones into keto acids [555, 559, 590] or acids [559, 597], ethers into esters [555], and amines into amides [854, 555] or imines [557], Aromatic amines are oxidized to nitro compounds [755, 559, 592], aliphatic nitro compounds to ketones [562, 567], sulfides to sulfones [846], selenides to selenones [525], and iodo compounds to iodoso compounds [595]. 

Whereas internal acetylenes are oxidized to a-diketones, terminal acetylenes give carboxylic acids with one less carbon on treatment with thallium trinitrate [413], potassium permanganate [843], iodosobenzene with tris(triphenylphosphine)ruthenium dichloride as a catalyst [787], or a rather rare oxidant, pentafluoroiodobenzene bis(trifluoroacetate) [797] (equation 144). 

Acetylenic acids are oxidized to a-diketo carboxylic acids by potassium permanganate in aqueous solutions buffered to pH 7.0-7.5 by carbon dioxide (equation 475) [864]. 

Acetylene, like other unsaturated compounds, is readily oxidized by a solution of potassium permanganate. Oxalic acid, carbon dioxide, and other substances are formed as the result of the oxidation. 

Oxidation of Alkynes, Alkenes, and Benzylic Hydrocarbons. The yields of 1,2-diketones from the oxidation of acetylenes by potassium permanganate under aqueous conditions are substantially improved by buffering (pH 7—7.5) the reaction mixture.However, potassium permanganate-phase transfer catalyst in... 

Benzyltriethylammonium permanganate (c/. 3, 9 ) has been suggested as a mild oxidant suitable for converting aldehydes into acids/ but there are problems associated with the handling of this reagent (see refs. 169, 170). Disubstituted acetylenes are oxidatively cleaved to carboxylic acids by potassium permanganate, the nature of the products depending on the solvent mixture used yields are very respectable in a number of cases. ... 

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