Sulfonyl halides reduction

Reduction of Sulfonyl Halides and Sulfonic Acids to Thiols... 

Thiols can be prepared by the reduction of sulfonyl halides with LiAlHLj. UsualK the reaction is carried out on aromatic sulfonyl chlorides. Zinc and acetic acid, and... 

The Smiles rearrangement 5-28 Addition of ArSSCl to alkenes 9-35 Oxidation of thiols 9-54 Reduction of sulfonyl halides... 

Reduction of sulfonic odds to disulfides. This combination of reagents reduces aryl sulfonyl halides and sulfonic acids to disulfides in yields generally >90%. 

Reduction of sulfonyl halides to disulfides. Two laboratories 9 10 have reported the reduction of sulfonyl chlorides to disulfides by ISi(CH,), or ClSi(CH, ),-Nal in... 

Zinc salts of sulfinic acids are formed by reduction of sulfonyl chlorides by zinc and hot water. The zinc salts may be converted to sodium salts by the action of sodium carbonate. Over-all yields of the sodium salts of -toluenesulfinic acid and 2-dibenzofuransulfinic acid are 64-67%. Equally good results have been obtained by reduction of sulfonyl halides with aqueous sodium sulfite. Complete reduction to sulfhydryl compounds occurs with certain reducing agents (method 509),... 

Many other functional groups are reduced by Sml. For example, sulfonyl halides are converted to disulfides. The reduction of nitro compounds by this reagent enables synthesis of 1,2-diamines based on a reaction sequence initiated by nitronate addition to aldimines, and in the presence of nitriles it furnishes amidines, and that of isothiocyanates in the presence of conjugated esters, the half thioamide derivatives of succinic esters. 

REDUCTION OF SULFONYL HALIDES WITH ZINC POWDER S-METHYL METHANETHIOSULFONATE (Methanesulfonothioic acid, S-methyl ester)... 

S-Methyl methanethiosulfonate is commercially available, but is expensive. Other preparation methods involve oxidation of thiols or disulfides by halogens or peroxides,3 reduction of sulfinyl halides5 (which have to be prepared) or sulfonyl halides with potassium iodide6 or copper/bronze7 as well as thermolysis of sulfonylhydrazines.8 Finally, a two-day procedure for the preparation of methyl methanethiosulfonate has been reported from dimethyl sulfoxide.9... 

REDUCTION OF SULFONYL HALIDES WITH ZINC POWDER S-METHYL METHANETHIOSULFONATE. 

Although perfluorocarbon sulfonic acid groups are very stable chemically as well as thermally, perfluorocarbon sulfonyl halide, especially sulfonyl chloride groups, are quite reactive. For example, sulfonyl chloride groups react with oxidants, reductants, various amines, phenol compounds, iodine compounds, etc. and give carboxylic acid, sulfinic acid, sulfonic acid amide, -CF2I and so forth. Some examples of how this feature can be used to generate various kinds of membranes will next be described... 

Reaction with Sulfonyl Halides. Arylsulfonyl halides undergo reductive dimerization to form the corresponding disulfides (eq 35). Alkylsulfonyl halides, however, undergo this process under somewhat more vigorous conditions. Although sulfones generally do not react with TMS-I, certain cyclic sulfones are cleaved in a manner analogous to lactones. ... 

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