Oxone® potassium

Tetrahydrobenzyl alcohol (( )3-cyclohexenene-l-methanol) and 30% aqueous hydrogen peroxide were purchased from Fluka, AG. 3-Cyclohexene-1-carboxylic acid and cis-4-cyclohexene-l,2-dicarboxylic acid were used as purchased from Lancaster Chemical Co. Methyl iodide, acetic anhydride, Oxone (potassium peroxymonosulfate), Aliquot 336 (methyl tri-n-octylammonium chloride), sodium tungstate dihydrate and N,N-dimethylaminopyridine (DMAP) were purchased from Aldrich Chemical Co. and used as received. 3,4-Epoxycyclohexylmethyl 3, 4 -epoxycyclohexane carboxylate (ERL 4221) and 4-vinylcyclohexene dioxide were used as purchased from the Union Carbide Corp. (4-n-Octyloxyphenyl)phenyliodonium hexafluoroantimonate used as a photoinitiator was prepared by a procedure described previously (4). 

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. 

It is noteworthy that quick and effective formation of diaryl nitrones can be achieved through oxidation of diaryl imines with Oxone (potassium peroxy-monosulfate) in such media as aqueous solution of NaHCC>3 in acetonitrile or acetone. When oxidized under such conditions, dialkyl or monoaryl imines give oxaziridines (17). Oxidation of 3,4-dihydroisoquinoline (9) with Oxone initially leads to the formation of oxaziridine (10) which is easily transformed into the corresponding 3,4-dihydroisoquinoline A-oxide (11) upon treatment with catalytic amounts of p-toluenesulfonic acid (Scheme 2.4) (18). 

As oxiranes can be generated in situ from Oxone (potassium peroxomono-sulfate) and a ketone, dioxiranes are attractive oxidants for epoxidation reactions that may be rapid and may require only a simple workup. 

Oxone (potassium peroxymonosulfate, 2 KHSO5KHSO4K2SO4) was purchased from Aldrich Chemical Company, Inc. 

Sulfides in the electrophilic positions are often oxidized to sulfones to facilitate nucleophilic displacement reactions. The sulfoxide is initially formed, and can sometimes be isolated, but normally the oxidation is allowed to proceed fully to give the sulfone. Peroxyacids are commonly used as the oxidant, although other reagents such as oxone (potassium peroxymonosulfate) can also be employed <20030L1011, 2006ARK(vii)452>. 

Chiral ketone-catalyzed asymmetric epoxidation has received intensive interest since the first reported by Curci et al. in 1984. The reaction is performed with oxone (potassium peroxomonosulfate) as the primary oxidant which generates the chiral dioxirane catalytic species in situ, which in turn, transfers the oxygen... 

Reaction of the ra-ene-5-yne carboxylic acid 977 with biscollidine iodine(l) hexafluorophosphate leads to exclusive formation of the C(6)-( )-iodovinyl tetrahydropyran-2-one 979. The product arises via attack of the acid onto the iodinium ion intermediate 978 (Scheme 258) <2004TL4503>. A similar iodolactonization of hex-5-enoic acid can be induced by Oxone -potassium iodide to furnish 6-(iodomethyl)tetrahydropyran-2-one in excellent yield (Equation 380) <2004SL368>. Similarly, treatment of 5-hexynoic acid with a polymer bound source of electrophilic iodide affords the tetrahydropyran-2-one 980 bearing a diiodo-substituted exocyclic double bond (Equation 381) <1999OL2101>. 

Catalytic oxidation of RtS to R S = 0.2 This sulfonamide can function as a catalyst for oxidation of sulfides selectively to sulfoxides by Oxone (potassium peroxymonosulfate). The net effect involves transfer of oxygen from an N-sulfon-yloxaziridine to the sulfide. This catalytic system is useful because sulfones are formed if at all only in traces. 

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... 

Dioxiranes are extremely useful reagents for the epoxidation of alkenes under neutral conditions. Since the oxygen atom transfer to the alkene regenerates the initial ketone, this epoxidation is catalytic. Dioxiranes are easily generated by the action of an oxone (potassium persulfate) on a ketone (usually acetone) either in a biphasic mixture or in a homogeneous aqueous organic solution. 

In the Shi epoxidation, an oxone (potassium persulfate, KOSO2OOH) in the presence of a fructose-derived catalyst, 7.57, generates epoxides with high enantiomeric excess oxone is best used to oxidize aldehydes to carboxylic acids in the presence of DMF. 

An efficient, high-yield synthesis of A-alkyl and A-aryl oxaziridine by oxidation of aldimines with buffered Oxone (potassium peroxymonosulfate) has been introduced by Hajipour and Pyne (Equation (47)) <92JCR(S)388>. Oxidation of the aldimine is accomplished in aqueous NaHC03/ acetonitrile or acetone affording the oxaziridine within 15-30 minutes in excellent yield (95-98%). The active oxidizing species in acetone and acetonitrile are thought to be dimethyldioxirane and peroxyimidic acid [MeC(OOH)=NH), respectively. 

Recent work with main group catalysts has concentrated on the use of Oxone (potassium peroxymonosulfate) as co-oxidant with organic ketone derivatives. Shing et al. have described an arabinose ketone catalyst containing a tuneable butanediacetal functionality (Fig. 1.2e) which can be used for asymmetric epoxidation with up to 90% ee [198]. The group of Shi reports on a range of ketones bearing... 

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]. 

OXONE = potassium peroxymonosulfate [2KHSO5.KHSO4.K2SO4]... 

Related Reagents. Potassium Monoperoxosulfate (Oxone) Potassium Monoperoxosulfate (Oxone)/Acetone (DDO in situ) Methyl(trifluoromethyl)Dioxirane. 

Alternative Names potassium caroate, potassium hydrogen persulfate, Oxone , potassium peroxymonosulfate. 

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