Sulfonic from disulfides

Sulfonic acids from disulfides s. 1, 485 RSSR 2 RSO3H... 

Dimethyl sulfoxide hydrogen bromide Sulfonic acids from disulfides with Og/KOH cf. 19, 126 with dimethyl sulfoxide in 0. G. Lowe, J. Org. Chem. 41, 2061 (1976) Me SO/HBr RSSR 2 RSO3H the presence of HBr s. 

Hydrogen per oxide sulfuric acid Sulfonic acids from disulfides... 

Sulfonic acid chlorides from disulfides via sulfinic acids s. 18, 561 SOgH SO2GI... 

General Reaction Chemistry of Sulfonic Acids. Sulfonic acids may be used to produce sulfonic acid esters, which are derived from epoxides, olefins, alkynes, aHenes, and ketenes, as shown in Figure 1 (10). Sulfonic acids may be converted to sulfonamides via reaction with an amine in the presence of phosphoms oxychloride [10025-87-3] POCl (H)- Because sulfonic acids are generally not converted directiy to sulfonamides, the reaction most likely involves a sulfonyl chloride intermediate. Phosphoms pentachlotide [10026-13-8] and phosphoms pentabromide [7789-69-7] can be used to convert sulfonic acids to the corresponding sulfonyl haUdes (12,13). The conversion may also be accompHshed by continuous electrolysis of thiols or disulfides in the presence of aqueous HCl [7647-01-0] (14) or by direct sulfonation with chlorosulfuric acid. Sulfonyl fluorides are typically prepared by direct sulfonation with fluorosulfutic acid [7789-21-17, or by reaction of the sulfonic acid or sulfonate with fluorosulfutic acid. Halogenation of sulfonic acids, which avoids production of a sulfonyl haUde, can be achieved under oxidative halogenation conditions (15). 

Sulfones are neutral and very stable compounds that can be distilled without decomposition. They are freed from acidic and basic impurities in the same way as disulfides. The low molecular weight members are quite... 

Sulfinic esters, aromatic, by oxidation of disulfides in alcohols, 46, 64 Sulfonation ot d,l camphor to d,l-10-camphorsulfomc acid, 45,12 Sulfoxides, table of examples of preparation from sulfides with sodium metapenodate, 46,79 Sulfur dioxide, reaction with styrene phosphorus pentachlonde to give styrylphosphomc diclilonde, 46,... 

A very surprising sulfone formation has been investigated by Oae and coworkers . On heating p-toluenesulfinic acid with dimethylaniline in ethanol for 15 h, the reaction mixture shown in equation 100 has been obtained. Obviously, the observed products arise from an equilibrium between the sulfinic acid and its pseudo-anhydride (disulfide trioxide), which is able to attack the amine nitrogen and degrade the tertiary amine corresponding to a Polonovsky reaction . 

Rhodococcus strain SY1 was reported to desulfurize dimethyl sulfide, dimethyl sulfoxide, and several alkyl sulfonates [41] in addition to DBT [78], Barium chloride has been used to precipitate sulfate and shown to alleviate sulfate repression partially. The authors proposed a tentative pathway for oxidative removal of sulfur from DBT and other organosulfur compounds. It should be noted that phenyl disulfide and thianaph-thene were not desulfurized by any of the Rhodococcus strains, but have been reported to be substrates of Gordonia CYKS2. 

Merox [Mercaptan oxidation] A process for removing mercaptans from petroleum fractions by extracting them into aqueous sodium hydroxide and then catalytically oxidizing them to disulfides using air. The catalyst is an organometallic compound, either a vanadium phthalocyanine supported on charcoal, or a sulfonated cobalt phthalocyanine. Developed by UOP in 1958 and widely licensed by 1994, more than 1,500 units had been built, worldwide. Unzelman, G. H. and Wolf, C. J., in Petroleum Processing Handbook, Bland, W. F. and Davidson, R. L., Eds., McGraw-Hill, New York, 1967, 3-128. 

In abroad sense, the model developed for the cobaloxime(II)-catalyzed reactions seems to be valid also for the autoxidation of the alkyl mercaptan to disulfides in the presence of cobalt(II) phthalocyanine tetra-sodium sulfonate in reverse micelles (142). It was assumed that the rate-determining electron transfer within the catalyst-substrate-dioxygen complex leads to the formation of the final products via the RS and O - radicals. The yield of the disulfide product was higher in water-oil microemulsions prepared from a cationic surfactant than in the presence of an anionic surfactant. This difference is probably due to the stabilization of the monomeric form of the catalyst in the former environment. 

From the same zirconocene intermediates, Huang and co-workers have prepared vinyl sulfides [24,35] and sulfones [26] through use of the appropriate quenching agents (Scheme 4.6). Treatment of vinyl zirconocenes with an equivalent of a disulfide in THF at 60 °C affords, after work-up and purification, (E)-vinyl sulfides in good isolated yields. Vinyl sulfones, which as a class are generally useful as Michael acceptors and Diels—Alder dienophiles, are obtained in about two hours upon treatment of (fc)-vinyl zirconocenes with various sulfonyl chlorides in THF at 40°C. 

In contrast to the other large cats, the urine of the cheetah, A. jubatus, is practically odorless to the human nose. An analysis of the organic material from cheetah urine showed that diglycerides, triglycerides, and free sterols are possibly present in the urine and that it contains some of the C2-C8 fatty acids [95], while aldehydes and ketones that are prominent in tiger and leopard urine [96] are absent from cheetah urine. A recent study [97] of the chemical composition of the urine of cheetah in their natural habitat and in captivity has shown that volatile hydrocarbons, aldehydes, saturated and unsaturated cyclic and acyclic ketones, carboxylic acids and short-chain ethers are compound classes represented in minute quantities by more than one member in the urine of this animal. Traces of 2-acetylfuran, acetaldehyde diethyl acetal, ethyl acetate, dimethyl sulfone, formanilide, and larger quantities of urea and elemental sulfur were also present in the urine of this animal. Sulfur was found in all the urine samples collected from male cheetah in captivity in South Africa and from wild cheetah in Namibia. Only one organosulfur compound, dimethyl disulfide, is present in the urine at such a low concentration that it is not detectable by humans [97]. 

Plant. In plants, fonofos is oxidized to the phosphonothioate (Hartley and Kidd, 1987). Oat plants were grown in two soils treated with [ C]fonofos. Most of the residues remained bound to the soil. Less than 2% of the applied [ C]fonofos was recovered from the oat leaves. Metabolites identified in both soils and leaves were methyl phenyl sulfone, 2-, 3- and 4-hydroyxymethyl phenyl sulfone, thiophenol, diphenyl disulfide, and fonofos oxon (Fuhremann and Lichtenstein, 1980 Lichtenstein et al., 1982). 

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