Potassium monoperoxysulfate

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

Solubility sol water (25.6 g 100 g, 20 °C), aqueous methanol, ethanol, acetic acid insol common organic solvents. 

Form Supplied in white, granular, free flowing solid. Available as Oxone and as Curox and Caroat . 

Analysis of Reagent Purity iodometric titration, as described in the Du Pont data sheet for Oxone . 

Handling, Storage, and Precautions the Oxone triple salt 2KHS05-KHS04-K2S04 is a relatively stable, water-soluble form of potassium monopersulfate that is convenient to handle and store. Oxone has a low order of toxicity, but is irritating to the eyes, skin, nose, and throat. It should be used with adequate ventilation and exposure to its dust should be minimized. Traces of heavy metal salts catalyze the decomposition of Oxone. For additional handling instructions, see the Du Pont data sheet. 

Hydroxylation of Ketones. Treatment of the ketone (4) with KOH in warm DMSO in the presence of O2 followed by the in situ reduction of the intermediate hydroperoxide with dithionite gave (5) as a 1 1 mixture of diastereomers (eq 4).  

Synthesis of ( )-j8-(Benzylo3gf)slyrenes from Ben l Alcohols. ( )-/3-(Benzyloxy)styrenes (7) were obtained from the reaction of benzyl alcohols (6) with KOH/DMSO (eq 5) in 56-92% yields. This result was explained by an initial oxidation to the benzaldehyde followed by a condensation with DMSO anion to form intermediate (8). Subsequent addition of benzyloxide anion to (8) and elimination of MeSO gives the product (7). The incorporation of the DMSO carbon was confirmed by and labelling. The methyl styryl sulfoxide intermediate (8) was independently synthesized and converted into (7) under identical reaction conditions.  

Preparation of Af-Vinylpyrroles. The reaction of ketoximes having at least one a-CHa group with acetylene in DMSO/KOH at 80-120 °C under atmospheric pressure gave (V-vinylpyrroles in average yields of 70-80% via an intermediate pyrrole (eq 6). The conditions are also suitable for AAvinylation of pyrroles and other NH heterocycles in good yields.  

For discussions of the behavior of KOH in polar aprotic solvents see (a) Jolly, W. L., J. Chem. Educ. 1967, 44, 304. (b) Trofimov, B. A., Russ. Chem. Rev. (Engl. Transl.) 1981, 50,138 and references therein. 

Ahmed F. Abdel-Magid The R. tv Johnson Pharmaceutical Research Institute, Spring 

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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. 

Dimethyldioxirane has also been used as the epoxidizing agent in a key step in the synthesis of A-norsteroids69,70. The reaction occurs in dichloromethane-acetone and is highly regio- and stereoselective as shown in equation 9. Dioxiranes may also be generated in situ, by reaction of potassium monoperoxysulfate (sold commercially as OXONE) and cyclohexanones. In this case, cyclohexene derivatives may be smoothly epoxidized in 40-100% yields (equation 10)71. 

Several oxidants (Fig. 1) are used as the oxygen source. Examples are bleach (NaOCl), hydrogen peroxide (H202), organic peroxides like dimethyldioxyrane (DMD) or ferf-butyl hydroperoxide (TBHP), peracids like m-chloroperbenzoic acid (mCPBA) or potassium monoperoxysulfate (KHSO5). 

Treatment of (1) with Potassium Monoperoxysulfate (oxone) gave an 80% yield of the exo-epoxide (4) (eq 3), which is of potential use for the preparation of carbocyclic analogs of 2 -or 3 -deoxyribofuranosylamines. 

Preparative Methods the enantiopure (+)- and (—)-(cam-phorylsulfonyl)oxaziridines (1) and [(8,8-dichlorocam-phor)sulfonyl]oxaziridines (2) are commercially available. They can also be prepared on a large scale via the oxidation of corresponding camphorsulfonimines with buffered Potassium Monoperoxysulfate (Oxone) or buffered peracetic acid. Since oxidation takes place from the endo face of the C=N double bond, only a single oxaziridine isomer is obtained. The precursor camphorsulfonimines can be prepared in 3 steps (>80% yield) from inexpensive (+)- and —yiO-Camphorsulfonic Acids. A variety of (camphorylsul-fonyl)oxaziridine derivatives such as (2)-(4) are also readily available via the functionalization of the camphorsulfonimines followed by oxidation. " ... 

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]. 

A NEW BRIGHT CHEMILUMINESCENT REACTION INTERACTION OF ACETONE WITH SOLID-PHASE POTASSIUM MONOPEROXYSULFATE IN THE COMPLEX OF EUROPIUM NITRATE... 

The need to prepare DDO solutions beforehand, the low yield of the reagent based on Potassium Monoperoxysulfate (Oxone) (ca. 5%), and tbe inconvenience of making DDO for large-scale reactions are drawbacks that can be avoided when the product has good stability. In these instances, an in situ metbod for DDO oxidations is recommended. 

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