Nucleophilic Substitution of Nitroaromatic Halides by Electrogenerated Polysulphide Ions in Dimethylacetamide

DOI: 10.1039/P29910000817

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 817 - 823 (1991)

Update date:2022-08-02

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Authors:

Benaichouche, Meriem

Bosser, Gerard

Paris, Jacky

Plichon, Vincent

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Article abstract of DOI:10.1039/P29910000817

Electrogenerated polysulphide ions S₃^.- and S₈^2- 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 S_NAr mechanism implies that the dianions S₆^2- and S₈^2- are the nucleophilic agents (S₆^2- >> S₈^2-) rather than the S₃^.- and S₄^.- radical anions.

Full text of DOI:10.1039/P29910000817

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