Oxone® potassium compounds

The triple salt is better known by the trademarks Caroat (Degussa), OXONE Monopersulfate Compound (Du Pont), and Curox (Laporte). It is also known as potassium caroate. It has been made on a commercial scale siace the 1950s, and the world market ia 1994 was several thousand tons. It is made commercially by Peroxid-Chemie (Germany), Degussa (Germany), Du Pont (United States), and Migas (Japan). In 1994, the United Kingdom price was J1.80/kg ( 2.67/kg). 

The simplest model compound is cyclohexene oxide III. Monomers IV, V and VII represent different aspects of the ester portion of I, while monomers VII and VIII reflect aspects of both the monomer I and the polymer which is formed by cationic ring-opening polymerization. Monomers IV-VII were prepared using a phase transfer catalyzed epoxidation based on the method of Venturello and D Aloisio (6) and employed previously in this laboratory (7). This method was not effective for the preparation of monomer VIII. In this specific case (equation 4), epoxidation using Oxone (potassium monoperoxysulfate) was employed. 

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... 

There are other oxidants reported. The combination of m-CPBA and N-me thy I-morpholine-N-oxide is an effective anhydrous oxidant system for enantioselective oxidation with Mn(salen) compounds [224,225]. Dimethyldioxirane is prepared by the reaction of Oxone (potassium monoperoxysulfate) with acetone [317] and is a member of the smallest cyclic peroxide system. It is an active oxidant for a variety of olefins [318,319]. 

Works on the oxidation of uric acid has unequivocally established the triazine structure > ° (9) of oxonic acid. This is further confirmed by the straightforward synthesis described by Piskala and Gut. ° The reaction of biuret (11) with potassium ethyloxalate yielded a potassium salt (24), that with ethyl oxamate, the amide of oxonic acid (25). Both these compounds were converted to 5-azauracil. An analogous reaction with diethyloxalate which should produce an ester of oxonic acid resulted in a mixture of urethane and parabanic acid, however. 

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>. 

The one-pot conversions of oximes to gem-halonitro compounds have been achieved by using A(/V,/V.-trihalo-l,3,5-triazines,131 chloroperoxidase in the presence of hydrogen peroxide and potassium chloride,132 or commercial OXONE and sodium chloride.133 Of these methods, the case of OXONE may be the most convenient (Eq. 2.65). 

Relatively rare reactions are chemical oxidations of secondary alcohols to ketones by derivatives of hydrogen peroxide potassium peroxymono-sulfate (Oxone) [205] and m-chloroperoxybenzoic acid [276]. These compounds do not offer any advantages over more-common oxidants. 

Oxidants suitable for the partial oxidation of amines to nitroso compounds are peroxy acids Caro acid, which is prepared in situ from potassium persulfate and sulfuric acid [195, 199 potassium peroxysulfate (Oxone) [295] peroxyacetic acid [i53], and peroxybenzoic add [1186], 3-Nitro-o-toluidine [195] and 5-nitro-o-toluidine [199] in aqueous-alcoholic solutions, when treated with a mixture of potassium persulfate and concentrated sulfuric acid, give 3-nitro-2-nitrosotoluene and 5-nitro-2-nitrosotoluene in respective yields of 60 and 55-66%. Organic peroxy acids convert 2,6-dihaloanilines into 2,6-dihalonitrosobenzenes (equation 497) [753, 1186]. p-Phenylenediamine (1,4-diaminobenzene) is oxidized by Oxone (2KHS05 KHS04 K2S04) in an aqueous suspension at room temperature to p-dinitrosobenzene in a quantitative yield [205]. 

Stability of oxidizers is also a concern. Halogenated products generate chlorine and bromine. Both are irritating, poisonous gases. Other materials decompose with the production of less objectionable elements or compounds. For example, the relatively stable potassium monopersulfate (Oxone), emits oxygen when it decomposes but at elevated temperatures, may also generate sulfuric acid, sulfur dioxide, or sulfur trioxide [6.3.2.3]. Small amounts of moisture (and, depending on the product, many other chemicals) reduce the stability of all oxidizers. 

A variety of alkenes undergo azidoiodination with sodium azide, potassium iodide, and Oxone on wet alumina to give azido-iodo compounds regioselectively in high yield (eq 79). These compounds are useful precursors to vinyl azides, amines, and aziridines and are typically synthesized with more expensive and exotic reagents. Similar methods have been used in the iodolac-tonization and iodoetherification of unsaturated carboxylic acids and alcohols to make five- and six-membered lactones, tetrahy-drofurans, and tetrahydropyrans (eq 80). ... 

The epoxidation of PBD with dimethyl dioxirane (DMD) as the oxidizing species shows that the epoxidation proceeds as expected with high stereoselectivity cis double bonds give c -epoxides. The latter was confirmed by NMR spectroscopic analysis. DMD can be prepared by conversion of acetone with Oxone, a potassium monopersulfate compound (Scheme 9). Prepared in situ or purified by distillation, DMD is an efficient oxidizing species for polydienes (Scheme 10) [127, 130]. 

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