Arenesulfinic acids

Arenesulfinic acid, from ArNj 241 Aromaticity of boron hydrides 283 Arseno-de-diazoniation 275 Aryl anions 211... 

Preparation of enantiomerically pure sulfmate esters has most often been accomplished by making menthyl esters of arenesulfinic acids, particularly of p-toluenesulfinic acid. This... 

The acidity of sulfinic acids is quite substantial. Benzenesulfinic acid has a pAg-value of 1.2 in water (Ritchie et al., 1961). Aliphatic sulfinic acids are somewhat weaker (p/fa = 2.2-2.3) (Rumpf and Sadet, 1958 Wudl et al., 1967). For the ionization of a series of arenesulfinic acids ArS02H in water pis +0.97 (Ritchie et al., 1961). 

Autoxidation of arenesulfinic acids to sulfonic acids has also been explored mechanistically (Horner and Basedow, 1958). The apparent mechanism is shown in (101)—(103). 

Complexes such as (6) have been postulated as intermediates in the PdCl2-catalyzed dimerization of arenesulfinic acids or their sodium salts to give the corresponding organic biaryls.36... 

Rhodococcus equi has been used for oxidation of sulfinic acid (Figure 33(b)).Mb Incubation of racemic arenesulfinic acid esters with the bacterial strain gave the corresponding sulfonates leaving optically pure (f )-substrate (>99% ee). 

Arenesulfinic acids.1 Oxidation of arenethiols generally results in mixtures of... 

The [3 + 2] addition of type IIbd is a significant method for synthesis of both simple and complex pyrrole derivatives. One manifestation of this pattern is seen in the base-catalyzed condensation of tosylmethyl isocyanide with alkenes having strong electron-accepting substituents. The aromatization by elimination of the arenesulfinic acid occurs under the reaction conditions (equation 117) (72TL5337). This reaction can be applied to the synthesis of 2,3,4-trisubstituted pyrroles by using C-alkylated tosylmethyl isocyanides or AT-tosyl-methyl-51-methylthioimidates (77H(7)77, 8IJHCII27). 

The reaction of palladium(II) complexes with arenesulfinic acids or their salts to yield the organic biaryls appears to proceed by formation of palladium sulhnato compounds and their desulfination 53a). 

Via thermolysis of bismuth sulfinates (method L) Thermolysis of bismuth tris(arenesulfinate), which can be prepared from bismuth acetate and arenesulfinic acid in glacial acetic acid, leads to the formation of triarylbismuthines [72AJC2107]. 

Unsaturated ketones68 and sulfinic acids afford y-oxo sulfones and (arylsulfonyl)hydroquinones are formed from quinones and arenesulfinic acids by 1,4-addition. According to work by Hinsberg and others69 occurrence of this reaction is direct evidence of a quinonoid structure if ortho- or para-positions are free and neither hydroxyl nor amino groups are present as substituents in the quinone. 

Arenesulfinic acid stannyl esters from arylstannanes... 

The nucleophilic addition of arenesulfinic acids to heteroconjugated alkenes, producing sulfones, has been found to proceed with second-order kinetics. ... 

Arenesulfinic acids have also been reported to add to 1,3-dienes in the presence of (1) and Ph3P to yield allylic sulfones (eq 25). ... 

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