Potassium hydrogen persulfate oxidation

Selective oxidation of either the aromatic ring or the side chain can also be accompHshed. For example, epoxidation of the double bond of cinnamic acid is effected in excellent yield by treatment with potassium hydrogen persulfate (10). 

The regeneration of carbonyl compounds from 1,3-dithianes can be achieved using potassium hydrogen persulfate, Oxone , supported on wet alumina <96SL767> and by periodic acid under non-aqueous conditions <96TL4331>. The deprotection of benzyl substituted 1,3-dithianes can be achieved using the one electron oxidant [Fe(phen)3](PF6)3 <96SL315>. 

Epoxidation Catalyzed by Metalloporphyrins. Metalloporphyrins, which have thoroughly studied as catalysts in alkane oxygenations, have also been tested as epoxidation catalysts.119,122,244,245,307 Iodosylbenzene (PhIO), sodium hypochlorite, alkyl hydroperoxides, potassium hydrogen persulfate, and molecular oxygen are the oxygen sources used most frequently in these oxidations.119... 

The desilylated products 31 and 32 (Scheme 20) were obtained by the protiodesilylation of a number of thioacylsilane adducts and the corresponding sulfones obtained by oxidation of the cycloadducts with oxone (potassium hydrogen persulfate). Compounds 31 are formally derived from unstable thioaldehydes and the cyclic sulfones 32 from thioaldehyde 5,5-dioxide (sulfenes) (Scheme 20). It should be noted that sulfenes produced by dehydrochlorination... 

The most widely used and, presumably, the most chemoselective reagents for the epoxidation of nucleophilic C—C double bonds are the peroxycarboxylic acids (see Houben-Weyl, Vol. IV/ 1 a, p 184, Vol. Vl/3, p 385, Vol. E13/2, p 1258). Using chloroform as solvent, epoxidation rates are particularly high79. Reactive or acid/base sensitive epoxides can often be obtained with dimethyldioxirane (see Houben-Weyl, Vol. R13/2, p 1256 and references 15, 16, 87-90), peracid imides (see Houben-Weyl, Vol. IV/1 a, p 205, Vol. VI/3, p 401, Vol. E13/2, p 1276) (prepared in situ from nitriles and hydrogen peroxide), hydroperoxy acetals (see Houben-Weyl, Vol. El3/2, p 1253) or peroxycarbonic acid derivatives (see Houben-Weyl, Vol. IV/la, p 209 and references 17-19) as oxidants. For less reactive alkenes, potassium hydrogen persulfate is a readily available reagent for direct epoxidation20. 

Oxone (a mixture of potassium sulfate, potassium hydrogensulfate and potassium hydrogen persulfate) is a commercially available oxidant which is generally used in aqueous ethanol. Oxone is highly chemoselective and will cleanly oxidise sulfides containing other functional groups for example, keto, hydroxy and alkenic double bonds are not attacked by this reagent. 

Potassium dichromate, 3 24 Potassium diisopropylamide, 324 Potassium ethanethiolate, 325 Potassium fluoride, 279, 325-326 Potassium formate, 329 Potassium-Graphite, 326 Potassium hexamethyldisilazide, 326-327 Potassium hydride, 327-328 Potassium hydrogen persulfate, 328 Potassium hydroxide-Alumina, 328 Potassium iodide-Boron(ill) iodide, 329 Potassium iodide-Zinc-Phosphorus(V) oxide, 329... 

Nickel peroxide. Oxoperoxobis(N-phenylbenzohydroxamato) molyb-denum(VI). Palladium(II) acetate-Tri-phenylphosphine. Palladium /-butyl peroxide trifluoroacetate. Periodic acid. Permonophosphoric acid. Potassium dichromate. Potassium hydrogen persulfate. Pyridinium dichromate. Ruthenium tetroxide. Selenium dioxide. Sodium hypochlorite. Titanium(IlI) chlo-ride-Hydrogen peroxide. Potassium nitrodisulfonate. Potassium peroxodi-sulfate. Pyridinium chlorochromate. Pyridinium chlorochromate-Hydrogen peroxide. Sodium permanganate monohydrate. Tetra-n-Butylammonium periodate. Thailium(III) acetate. Trimethyl-amine N-oxide. Triphenylmethylphos-phonium permanganate. 

Oxidation of Sulfoxides. Dialkyl, alkyl aryl, and diaryl sulfoxides are readily oxidized to sulfones in excellent yields under mild conditions (—30 °C) in MeCN by the peroxy intermediate (1). Oxidation of the unsaturated sulfoxide (11) was chemose-lective it furnished the sulfone (12) in 70% yield when reacted with (1) for 5 h. The double bond was not epoxidized. Similar chemoselective epoxidation has been carried out with only one other reagent (potassium hydrogen persulfate). ... 

Indfcan (Metabolic Indican). iH-lndol-3-ol hydrogen sulfate ester indot-3-yl Sulfate 3-indoxylsulfuric acid. C.H,NO,S mol wt 2]3,23. C 45.06%, H 3.31%, N 6.57%, O 30.01%, S 15.04%. Unstable as the free acid. Occurs in urine of mammals, also in blood plasma. Prepn of potassium salt from potassium indoxyl and potassium bisul fate Baeyer, Ber. 14, 1745 (1881) from chlorosulfonic acid and N-acetylindoxyl in pyridine Schwenk, Jolles, Biochem. Z. 69, 467 (1915) by persulfate oxidation of indole Boy-land el aL, Biochem. J. 62, 546 (1956). 

The most suitable oxidizing agent is potassium ferricyanide, but ferric chloride, hydrogen peroxide ia the presence of ferrous salts, ammonium persulfate, lead dioxide, lead tetraacetate or chromate, or silver and cupric salts may be useful. Water mixed, eg, with methanol, dimethylformamide, or glycol ethers, is employed as reaction medium. 

Many methods for the oxidative cyclization of 2-aminophenones to 2,1-benzisoxazoles have been reported and these were extensively discussed by Wiinsch and Boulton (67AHC(8)277). An illustrative reaction is the treatment of an aminophenone with hydrogen peroxide or potassium persulfate to produce 2,1-benzisoxazoles (Scheme 181) (64USP3261870). 

In the early studies on luminol and related hydrazides the systems used were composed of either sodium or potassium hydroxide, as base, hydrogen peroxide as the oxidizing agent (more recently molecular oxygen, hypochlorite, iodide, and permanganate have also been used), and some type of initiator or activator. This initiator was frequently hypochlorite, persulfate, a transition metal... 

Wet oxidation Several types of liquid-phase oxidizing agents, such as nitric acid, acidic potassium permanganate, acidic potassium dichromate, dichromate permanganate, hydrogen peroxide, ammonium bicarbonate and potassium persulfate, have... 

---