Journal of the Chemical Society. Perkin transactions II p. 817 - 823 (1991)
Update date:2022-08-02
Topics:
Benaichouche, Meriem
Bosser, Gerard
Paris, Jacky
Plichon, Vincent
Electrogenerated polysulphide ions S3.- and S82- readily react with haloaromatics, ArX, activated by nitro electron-withdrawing substituents in dimethylacetamide.Nucleophilic substitutions on fluoro-2,4-dinitrobenzene (1a; X = F), halo-4-nitrobenzenes (2a; X = F, Cl, Br, I) and 2-nitrobenzenes (3a; X = F, Cl, Br, I) lead to the coloured arylmonosulphide (1b; X = S-) and aryldisulphide (2c-3c; X = S2-) ions.From the reaction kinetics studied by UV-VIS spectrophotometry, the order of reactivity is ArF > ArBr >, ArI > ArCl.The proposed SNAr mechanism implies that the dianions S62- and S82- are the nucleophilic agents (S62- >> S82-) rather than the S3.- and S4.- radical anions.
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