Sodium arylsulfinates, reactions

Scheme 13 Reaction of ( )-alkenylbismuthonium salts with sodium arylsulfinates [37]...

The apparent SN reactions of chlorosulfines with sodium arylsulfinates to give sul-fonylsulfines with inversion of configuration in high yield was suggested to proceed via an addition-elimination mechanism rather than an SN2 mechanism.58... 

Although the reaction of 1,2-dichloro-3,3-difluorocyclopropene with thiocyanate leads simply to the replacement of the two chlorines by the nucleophile, reaction of the cyclopropene or of tetrachlorocyclopropene with sodium arylsulfinates gave an alkene in low yield (< 10%), apparently via the cyclopropenone, e.g. reaction of I. ... 

Small amounts of water act in synergy with sonication and solid-support catalysis, for instance, in the reaction of thiocyanate ions. As in the previous case, presonication of the reagent and the support was found to improve the selectivity. These methods permit the substitution reactions to be run even in apolar solvents. Two practically simultaneous papers have described the preparation of aryl sulfones by alkylation of sodium arylsulfinates with reactive alkyl chlorides.i The reaction with benzyl chlorides is best performed on alumina, and allyl bromide reacts quantitatively in a DMF-water mixture in a few minutes. Activated primary halides undergo substitution by sodium azide in aqueous solution to give the potentially explosive organic azides. 1 The paper discusses the possible role of the relative densities of the starting material, the aqueous solution of the reagent, and the product in the success of the preparation. 

A novel and convenient Pd-catalysed desulfitative cross-coupling reaction of sodium arylsulfinates (346) with diallq l phosphites has been developed. This highly efficient method provided a rapid access to a... 

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