Sulfonic acids 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... 

The end product of the oxidation of mercaptans, sulfides, disulfides, sulfoxides, sulfones, etc., is a sulfonic acid. From a preparative stand-... 

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). 

The sulfonyl group is a key feature in the preparation of the unusually substituted dithiin sulfone (174) from dibenzyl sulfone. The acidic a-protons are abstracted with sodium hydride and the carbanionic intermediates react with carbon disulfide. The reaction is quenched with methyl iodide to give (174) in 17% yield (73BSF637). Another multisubstituted dithiin (175) is available from the reaction of diphenylthiirene dioxide with the ylide (176) (Scheme 21) but again the yield is low. However, the reaction is of particular interest in so far as the product mixture also contains a derivative of the rare oxathiin nucleus. Indeed of the three products isolated the oxathiin sulfone (177) is formed in marginally the highest yield (73BCJ667). 

A very convenient method has been devised [40] for the conversion of thiols to ethyldithio derivatives as a routine procedure for protection of thiol-substituted organic acids. It uses a DMAP-catalysed exchange of the ethylthio group between a thiol and ethyl 2-pyridyl disulfide, prepared from the commercially available 2,2 -dithiobispyridine. Filtration through a macroporous sulfonic acidic resin and evaporation of the solvent yielded the disulfide directly. 

Sulfur compound VIII, a carboxytrimethylbenzene sulfonic acid, could have come from an aryl disulfide, a thiol or could be derived from the further oxidation of compound IX, a carboxytrimethyldibenzothiophene-1,1-dioxide. This latter possibility is indicated by the lower concentration of compound IX relative to compound VIII in the oxidation products of coals containing mineral matter. Once again the catalytic effect of the mineral component of coal is indicated. 

Thiazolyl sulfamic acids, rearrangement of sulfonic acid, 70 rearrangement to sulfonic acid, 75 by sulfonation, 75 2-Thiazolyl sulfenyl chloride, transformation to, thiazolyl disulfides. 412 2-Thiazolyl sulfide, in hydrocarbon synthesis, 406 oxidation of, with m-chloroperbenzoic acid, 415 with CrOj, 415 with Hj02,405,415 with KMn04,415 physical properties, infrared, 405 NMR, 404 pKa, 404 ultraviolet, 404 preparation of, from 2-halothiazoles and 5-Thiazolyl sulfides, bis-5-thiazolyl sulfide, oxidation of, 415 general, 418 5-(2-hydroxythiazolyl)phenyl sulfide case, 418 physical properties, 418 preparation of, 417-418 table of compounds, 493-496 uses of. 442 2-Thiazolyl sulfinic acid, decomposition of, 413 preparation of, from 2-acetamidothiazole sulfonyl chloride, 413 from A-4-thiazoline-2-thione and H, 0, 393,413 table of compounds, 472-473 5-Thiazolyl sulfinic add, preparation of,... 

Orthanilic acid was first made by the reduction of nitro-benzenesulfonic acid by ammonium sulfide.2 This reduction has also been carried out electrolyticallv, and by the use of iron or zinc.3 The acid has also been made by the rearrangement of phenylsulfamic acid,4 by the action of sodium hypobromite upon potassium o-carbaminebenzenesulfonate,5 by the reduction of the mixed nitrobenzenesulfonic acids followed by separation of the isomers,6 by the action of methyl alcohol upon o-nitro-phenylsulfurchloride,7 by the action of acid upon diacetyl diphenylsulfamide,8 by the debromination of />-bromoaniline-e-sulfonic acid,9 by the reduction of 1,2,6-aminothiophenolsulfonic acid,10 and by the hydrolysis and reduction of e-nitrobenzene-sulfonyl chloride, which was obtained from di-o-nitrophenyl-disulfide.11... 

This method is a modification of that of Buckles, Hausman, and Wheeler.2 4,4 -Dibromobiphenyl has also been prepared by the bromination of biphenyl in water,3 carbon disulfide,4 and glacial acetic acid 6 by the bromination of a mixture of biphenyl-sulfonic acids in dilute sulfuric acid 6 by the action of sodium carbonate on the perbromide obtained from the reaction of di-azotized benzidine with bromine water 7 and by passing />-di-bromobenzene vapor through a red-hot tube.8... 

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