Of sulfide to sulfone

Sulfones. This oxidant is useful for selective oxidation of sulfides to sulfones (10,328). Oxidations of acid-sensitive substrates should be buffered with Na2C03. 

Oxidation of sulfides and sulfoxides using Oxone dispersed on silica gel or alumina was reported . A study of surface mediated reactivity of Oxone compared its reactivity with that of ferf-butyl hydroperoxide. Oxidation of sulfides to sulfones in aprotic solvents mediated by Oxone on wet montmorillonite or clay minerals proceeds in high yields. Interestingly, when Oxone on alumina is applied for selective oxidation of sulfides in aprotic solvents, the product distribution is temperature-dependent and sulfoxides or sulfones are obtained in good to excellent yields (equation 56) . ... 

THE FIRST EXAMPLE OF DIRECT OXIDATION OF SULFIDES TO SULFONES BY AN OSMATE-MOLECULAR OXYGEN SYSTEM... 

The oxidation of sulfides to sulfones has been the subject of extensive studies, since sulfones are useful synthons for the construction of various chemically and biologically significant moleculesJ Recently, a new catalytic system has been developed by exchanging potassium osmate onto chloride-saturated layered double hydroxides (Figure 9.1), which we have shown to be an efficient catalyst for the direct oxidation of sulfides to sulfones, using molecular oxygen as the stoichiometric oxidant and with delivery of two oxygen atoms simultaneously to the sulfide, reminiscent of olefin dihydroxylation reactions. 

Sulfunes. A recent preparation of thietane 1,1-dioxide1 emphasizes the advantage of tungstic acid catalysis2 in the hydrogen peroxide oxidation of sulfides to sulfones an induction period is eliminated and the yield improved. 

Oxidation of sulfides to sulfones.[ Sulfides are oxidized chemoselectively to sulfones by KHSOs (3 equivalents) in high yield. Peracids are usually used for this oxidation, but can also oxidize olefinic groups. Oxidation of sulfides to sulfoxides is also possible with 1 equivalent of reagent. 

A recent method for the highly chemoselective oxidation of sulfides to sulfones using Af-methylmorpholine IV-oxide (NMP) and a catalytic perruthenatc was found to be also applicable in the presence of isolated or allylic double bonds [115]. 

Gokel, G.W., Gerdes, H.M., and Dishong, D.M., Sulfur heterocycles. 3. Heterogenous, phase-transfer, and acid catalyzed potassium permanganate oxidation of sulfides to sulfones and a survey of their carbon-13 nuclear magnetic resonance spectra, J. Org. Chem., 45, 3634, 1980. 

Sodium percarbonate (PCS) can also be employed for the oxidation of sulfides to sulfones in acetonitrile assisted by ultrasound.415... 

A number of other oxidants which produce sulfones from sulfoxides are known, such as N02BF4, ° oxygen with Ir or Rh catalysts, ozone,KHSOs (Oxone) and K2S20s. Oxone is a highly chemoselective oxidant for the conversion of sulfides to sulfones without affecting hydroxy or al-kenic groups (equation 37). Similarly flavin (14) oxidizes aryl methyl sulfoxides to sulfones fairly selectively. ... 

Peroxyphthalic add, o-C,iH4(C02H)C03H, is obtained from phthalic anhydride and hydrogen peroxide [330] or sodium hydrogen peroxide [331] and is applied usually in ethereal solutions to epoxidations [330, 332], the Baeyer-Villiger reaction [333, 334], and oxidations of sulfides to sulfoxides [163, 335] and sulfones [336, 337]. The oxidation of sulfides to sulfones takes precedence over epoxidation, as evidenced by the fact that unsaturated ketone thioacetals are oxidized to unsaturated disulfones [337]. 

Sodium hypochlorite is used for the epoxidation of double bonds [659, 691] for the oxidation of primary alcohols to aldehydes [692], of secondary alcohols to ketones [693], and of primary amines to carbonyl compounds [692] for the conversion of benzylic halides into acids or ketones [690] for the oxidation of aromatic rings to quinones [694] and of sulfides to sulfones [695] and, especially, for the degradation of methyl ketones to carboxylic acids with one less carbon atom [655, 696, 697, 695, 699] and of a-amino acids to aldehydes with one less carbon [700]. Sodium hypochlorite is also used for the reoxidation of low-valence ruthenium compounds to ruthenium tetroxide in oxidations by ruthenium trichloride [701]. 

Oxidation. lodosobenzene has been suggested as a reagent for the oxidation of sulfides to sulfones. Thus a solution of 12 g. of the thiodiglycol (1) in 50 ml. of water was heated on the steam bath with 1.15 equivalents of lodosobenzene for about 15 min., cooled, and filtered. After removal of the iodobenzene layer, the solution was... 

Based on the facile oxidation of sulfides to sulfones with Oxone, phenyl vinyl sulfone (a multipurpose synthetic reagent) can be obtained in three steps from 2-bromoethanol, that is, displacement with PhSH, oxidation, and dehydration (via mesylation). ... 

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