Replacement of sulfonyl groups

Sulfonates s. Acyl sulfonates. Metal —, Phosphonium —, Sulfonic acid esters Suifonation s. a. Replacement of hydrogen by sulfonic acid groups N-Sulfonation 17, 355 Sulfones Cs. a. Replacement of sulfonyl groups, C- and a-Sulfonyl. . . )... 

Replacement of sulfonyl groups by hydrogen 7-Diketones from oc-sulfonyl-7-diketones... 

Sodium amalgam disodium hydrogen phosphate Replacement of sulfonyl groups by hydrogen with Zn/MeCOOH cf. 29, 792 with Na-amalgam in the presence of Na2HP04 as buffer, also replacement of phenylthio groups, s. B. H. Trost et al., Tetrah. Let. 1976, 3477... 

Replacement of sulfonyl groups by amino and hydroxyl groups Partial replacement... 

Replacement of the sulfonyl group by a carbonyl group gave the tasteless, phthalimide analog (101). On the other hand, if the carbonyl groups are replaced by sulfonyl groups, to produce benzodithioimide (102),... 

Pyrazolesulfonic acids, like (493), have high melting points (Table 24) and probably exist as the zwitterions (497). They are very stable to hydrolysis and only afford pyrazolones at high temperatures. The replacement of the SO3H group by bromine has also been reported (B-76MI40402). Pyrazole-3-, -4- and -5-sulfonic acids react with phosphorus pentachloride to form sulfonyl chlorides. 

Diuretic activity can be retained in the face of replacement of one of the sulfonamide groups by a carboxylic acid or amide. Reaction of the dichlorobenzoic acid, 174, with chlorsulfonic acid gives the sulfonyl chloride, 175 this is then converted to the amide (176). Reaction of that compound with furfuryl ine leads to nucleophilic aromatic displacement of the highly activated chlorine at the 2 position. There is thus obtained the very potent diuretic furosemide (177). ... 

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