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Oxone synthesis

Ballini, R., Curini, M., Epifano, F., Marcotullio, M. C., Rosati, O. A new, modulated, oxidative ring-cleavage of a-nitro cycloalkanones by Oxone. Synthesis of a,co-dicarboxylic acids and a,to-dicarboxylic monomethyl esters. Syn/eff 1998, 1049-1050. [Pg.637]

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. [Pg.200]

Previous studies by Sorokin with iron phthalocyanine catalysts made use of oxone in the oxidation of 2,3,6-trimethylphenol [134]. Here, 4 equiv. KHSO5 were necessary to achieve full conversion. Otherwise, a hexamethyl-biphenol is observed as minor side-product. Covalently supported iron phthalocyanine complexes also showed activity in the oxidation of phenols bearing functional groups (alcohols, double bonds, benzylic, and allylic positions) [135]. Besides, silica-supported iron phthalocyanine catalysts were reported in the synthesis of menadione [136]. [Pg.101]

A convenient procedure for the lactonization of alkenols has been recently revealed by Borhan and coworkers [19]. This methodology was successfully applied in the total synthesis of (+)-tanikolide (7-37), a natural product of marine origin which exhibits antifungal activities. Thus, when alkenol 7-36 is subjected to soluble oxone and a catalytic amount of 0s04, a smooth domino oxidative cleavage/lactonization process takes place which leads, after debenzylation, to the desired product in good overall yield (Scheme 7.12). [Pg.501]

For the synthesis of the title compound, Oxone or 3-chloroperbenzoic acid2 can be used to oxidize the sulfide to the sulfone. The title compound is a key reagent for the preparation of fluoroalkenes from aromatic11 and aliphatic2 aldehydes. Recently, a stereospecific method to (E)- and (Z)-fluoroalkenes was reported using this reagant.12 13 14... [Pg.108]

Primary, secondary and tertiary aliphatic amines are efficiently converted to nitro compounds in 80-90 % yield with dimethyldioxirane, a reagent prepared from the reaction of oxone (2KHSO5-KHSO4-K2SO4) with buffered acetone. Dimethyldioxirane (DMDO) has been used for the synthesis of 1,3,5,7-tetranitroadamantane (71) from the corresponding tetraamine as the tetrahydrochloride salt (70) and is an improvement over the initial synthesis using permanganate anion (Table 1.7). ° Oxone is able to directly convert some aromatic amines into nitro compounds. [Pg.21]

Asymmetric epoxidation of olefins is an effective approach for the synthesis of enan-tiomerically enriched epoxides. A variety of efficient methods have been developed [1, 2], including Sharpless epoxidation of allylic alcohols [3, 4], metal-catalyzed epoxidation of unfunctionalized olefins [5-10], and nucleophilic epoxidation of electron-deficient olefins [11-14], Dioxiranes and oxazirdinium salts have been proven to be effective oxidation reagents [15-21], Chiral dioxiranes [22-28] and oxaziridinium salts [19] generated in situ with Oxone from ketones and iminium salts, respectively, have been extensively investigated in numerous laboratories and have been shown to be useful toward the asymmetric epoxidation of alkenes. In these epoxidation reactions, only a catalytic amount of ketone or iminium salt is required since they are regenerated upon epoxidation of alkenes (Scheme 1). [Pg.202]

Botta and coworkers recently developed an Oxone cleavage methodology for the solid-phase synthesis of substituted uracUs (equation 57) . Whereas some common methods of thioether cleavage, such as reduction with Na/NHs, acid catalyzed hydrolysis, heavy metal ions followed by treatment with hydrogen sulfide and iodofrimethylsilane proved to be unsuccessful for this reduction, Oxone was shown to be an efficient and selective reagent for cleavage of polymer bound thiouracUs. [Pg.1025]

In the attempted synthesis of isothiazolo[5,4-3]pyridin-3(2//)-one 1,1-dioxide 172, direct oxidation of isothi-azolo[5,4-/ ]pyridin-3(2//)-one with either Oxone /MeOH, 3-chloroperoxybenzoic acid/CH2Cl2, or KMn04/AcOH did not afford the desired product. However, this compound was synthesized in good yield by treatment of 173 with chlorine in aqueous HCl and subsequent reaction with ammonia in ethanol (Scheme 14) <1996T8947>. [Pg.477]

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. [Pg.709]

Tetraphenylphosphonium monoperoxysulfate can be prepared from Oxone and tetraphenyphosphonium chloride [57]. Synthesis of the iminium salt catalyst is described in the source paper (see [57]). [Pg.485]

Mechanism of Shi epoxidation was probed for synthesis of (+)-(R,R) epoxide 20 in the reaction of frans-2-methylstyrene 18 with peroxymonosulphate (Oxone) in the presence of catalyst 19, chiral ketone derived from fructose (Scheme 5).74... [Pg.170]

The heterocyclic hemi-aminal 44 was formed as a model for the synthesis of the marine alkaloids zoanthamine and zoanthenol and is derived from the cyclic imine formed by the reduction of an appropriated substituted azide <07H(72)213>. A pyrrolidine-fused azepine has been isolated from the venom of the ant Myrmicaria melanogaster and assigned as 45 based upon GC and FT-IR comparison with synthetic material <07JNP160>. The axially chiral doubly bridged biphenyl azepine 46 has been synthesised and used with oxone as an epoxidation catalyst in a biphasic system <070BC501>. [Pg.436]

Amide 266 was also used for the synthesis of 5 (Scheme 37),109 employing syn-epoxidation to afford 284 in 96% yield. Alternatively, alkaline hydrolysis of 266 furnished 281, which could be trichloroacetylated to afford alkene 282. Treatment of 282 with potassium peroxymonosulfate ( oxone ) formed the corresponding syn-epoxide 283 in 60% yield. Epoxide 284 proved resistant to acid but did undergo slow hydrolysis upon using 2 1 H20-TFA to afford in 1 1.6 ratio the desired product 285 (32%) and its isomer 286 (52%), which for further characterization were transformed into the corresponding peracetates 289 (93%) and 290 (90%). Under similar conditions,... [Pg.79]

This remains a developing area for the synthesis of chiral oxiranes and has attracted interest from several research groups. As with the use of dioxiranes (above), it is not necessary to form the reactive oxaziridinium salt rather, the epoxidation reaction can be mediated by the corresponding iminium salt and Oxone. [Pg.256]


See other pages where Oxone synthesis is mentioned: [Pg.223]    [Pg.46]    [Pg.906]    [Pg.155]    [Pg.224]    [Pg.317]    [Pg.1030]    [Pg.251]    [Pg.1030]    [Pg.67]    [Pg.15]    [Pg.103]    [Pg.527]    [Pg.172]    [Pg.277]    [Pg.149]    [Pg.348]    [Pg.147]    [Pg.403]    [Pg.404]    [Pg.281]    [Pg.555]    [Pg.223]    [Pg.16]    [Pg.300]    [Pg.262]    [Pg.210]    [Pg.273]    [Pg.659]    [Pg.660]    [Pg.662]   
See also in sourсe #XX -- [ Pg.243 ]




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