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DOI: 10.1039/A707562F (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1998, 607-610

Nucleophilic substitution of S-phenyl thiol esters by electrogenerated polysulfide ions in N,N-dimethylacetamide

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Abdelkader Ahrika, Meriem Anouti, Julie Robert and Jacky Paris

Abstract

The reactivity of electrogenerated S⅓– polysulfide ions S3˙– (⇌S62–) towards S-phenyl thiol esters RC(O)SPh [R = Me (1), Et (2), Pri (3)] has been followed by spectroelectrochemistry in N,N-dimethylacetamide at 24 °C. With 1 and 2 reactions readily lead to thiocarboxylate ions and phenyltetrasulfanide ions, PhS4–, from the nucleofugic benzenethiolate ions in presence of sulfur. With 3 kinetic studies imply that S62– species are the nucleophilic S⅓– agents rather than S3˙– radical anions in a second order rate process (k = 30 ± 3 dm3 mol–1 s–1).

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