Sulfinic acid salts

Aryl sulfones have been prepared from sulfinic acid salts, aryl iodides and Cul. Unactivated thiocyanation has been accomplished with charcoal supported copper(I) thiocyanate." ... 

Sulfinates, 72 182 titanium, 25 119-120 Sulfinic acid salts, 23 658 Sulfinol process... 

With Grignard reagents, sulfur dioxide reacts to form sulfinic acid salts ... 

Alkylation of Sulfinic Acid Salts Alkylsulfonyl-de-halogenation... 

Accordingly, sulfone 194 changed into the respective sulfinic acid salt 195 that after oxidation gave sulfonate 196 (92%). 

Monohalogenothiazoles, 567 nucleophilic substitution reactions, 322 with amines. 567 with ArSH, 567 with benzamide, 567 with OH", 567 with OR", 567 relative reactivities, 568 with SR", 567 with sulfinic acid salts, 567 with sulfonamide, 567 reactions, with alkyl halides, 574 with n-butyllithium, 573 with Gtignard reagents, 573 reeduction of, with nickel, 573 with zinc, 573... 

Aryl sulfones have been prepared from sulfinic acid salts, aryl iodides and Formation of thiocyanates from unactivated aryl halides has been accomplished with charcoal supported copper(l) thiocyanate. " The copper catalyzed reaction of Na02SMe and aryl iodides give the aryl methyl sulfone. " A similar synthesis of diaryl sulfones has been reported using a palladium catalyst. " ... 

Arenethiosulfonic esters can be cleaved to sulfinic acid salts and disulfides by alkali681 or by thiolates.682... 

Table 9.17 Copper/ligand catalyzed coupling between aryl halides and sulfinic acid salts.

CuOTf-catalyzed C-S bond formation allows the formation of arylmethyl- and diarylsulfones. The coupling between aryl iodides and sulfinic acid salts proceeds in DMSO in the presence of A(A7-dimethylethylenediamine to give the sulfones with variable yields (eq 124). ... 

Keywords Arylboronic acids, sulfinic acid salts, [bimJOTf (ionic liquid), Cu(OAc)2, room temperature, sulfonylation, aryl sulfones... 

Salts of thiols (170) or of sulfinic acids (171) react like the alkoxides, giving 4-alkylthio- or 4-alkylsulfono-substituted butyrates. Alkali cyanides give 4-cyanobutyrates (172), hydroxylamine gives a hydroxamic acid (173), and hydra2ine a hydra2ide (174). 

These acids are less stable, less soluble and less acidic than the corresponding sulfonic acids. The common impurities are the respective sulfonyl chlorides from which they have been prepared, and the thiolsulfonates (neutral) and sulfonic acids into which they decompose. The first two of these can be removed by solvent extraction from an alkaline solution of the acid. On acidification of an alkaline solution, the sulfinic acid crystallises out leaving the sulfonic acid behind. The lower molecular weight members are isolated as their metal (e.g. ferric) salts, but the higher members can be crystallised from water (made slightly acidic), or alcohol. 

Benzenesulfinic acid [618-41-7] M 142.2, m 84 , pK 2.16 (2.74). The acid is purified by dissolving the Na salt in H2O, acidifying to Congo Red paper with HCl and adding a concentrated soln of FeCl3 whereby Fe sulfinate ppts. Collect the salt, wash with a little H2O, drain, suspend in H2O and add a slight excess of 1.5M aq NaOH. The Fe(OH)3ppts, it is filtd off, the sulfinic acid in the aq soln is extracted with... 

Sulfin, n, sulfonium, sulfine, HaS. -farbe, /, -farbstoff, m. sulfur dye. -salz, n, sulfonium salt, sulfine salt. -sSure, /. sulfinic acid,... 

Addition of sulfinic acids (or salts) to unactivated C=C double bonds 172... 

An inverse addition of sulfinic acid to a thiocarbonyl group could have taken place with the reactive intermediate 8, which should arise from thiophosgene and methanesulfmic acid (sodium salt)106 (equation 28). The first step of this reaction represents an S-acylation... 

There are many parallels between phosphates and sulfates of aliphatic alcohols. Both types of surfactants contain ester bonds undergoing hydrolysis in acid solutions. In that case the starting materials are received once more. By dry heating of the salts above a temperature of 140°C destruction will occur forming the corresponding alkenes and an inorganic acid salt. In the same way as sulfonic and sulfinic acids are formed by C-S bonds, C-P bonds lead to phosphonic and phosphinic acids. 

Alkyl halides or alkyl sulfates, treated with the salts of sulfinic acids, give sulfones. A palladium catalyzed reaction with a chiral complexing agent led to sulfones with modest asymmetric induction. Alkyl sulfinates (R SO—OR) may be side products. Sulfonic acids themselves can be used, if DBU (p. 1337) is... 

Diazonium salts can be converted to sulfonyl chlorides by treatment with sulfur dioxide in the presence of cupric chloride. The use of FeS04 and copper metal instead of CUCI2 gives sulfinic acids (ArS02H). See also 13-18. 

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