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- W1997084942 abstract "The reactivity of electrogenerated polysulfide ions S3- (S62-) in N,N-dimethylacetamide has been followed by spectroelectrochemistry of a series of RC(O)X species: thioanhydrides X=SC(O)R (R=CH31a, C6H52a) and anhydrides X=OC(O)R (R=CH33b, n-C3H74b, t-C4H95b, C6H56b). With thioanhydrides two steps were evidenced: (i) formation of RC(O)S- in equilibrium with RC(O)S2- from both fast substitution at the trigonal carbon and exclusion from the nucleofugic anion X-: (ii) subsequent reaction of RC(O)S2- on substrates leading to diacyl disulfides. With anhydrides the first step only occurs at a slower rate. The electrolysis of sulfur in the presence of 1a or 2a allowed the preparative scale formation of RC(O)S2C(O)R as isolated products from the ‘electrochemical insertion of sulfur’ in diacyl monosulfides. Re′activite′ des ions polysulfures e′lectroge′ne′re′s dans le dime′thylace′tamide vis-à-vis des thioanhydrides et anhydrides d'acides carboxyliquesLa re′activite′ des ions polysulfures S3- (S62-) e′lectroge′ne′re′s dans le N,N-dime′thylace′tamide a e′te′ suivie par spectroe′lectrochimie vis-à-vis d'une se′rie de de′rive′s RC(O)X: thioanhydrides X=SC(O)R (R=CH31a, C6H52a), anhydrides X=OC(O)R (R=CH33b, n-C3H74b, t-C4H95b, C6H56b). Avec les thioanhydrides, deux e′tapes sont mises en e′vidence: (i) formation des ions RC(O)S- et RC(O)S2- en e′quilibre du fait de la substitution sur le carbone trigonal et de l'obtention de l'anion nucle′ofuge X-; (ii) re′action ulte′rieure des ions RC(O)S2- sur les substrats conduisant aux diacyldisulfures. Avec les anhydrides seule la première e′tape s'effectuant plus lentement est observe′e. L'e′lectrolyse du soufre en pre′sence des espèces 1a ou 2a re′alise′e au niveau pre′paratif a permis d'isoler les diacyldisulfures issus de ‘l'insertion e′lectrochimique du soufre’ sur les diacylmonosulfures." @default.
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- W1997084942 date "1998-01-01" @default.
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- W1997084942 title "Reactivity of electrogenerated polysulfide ions towards acyl thioanhydrides and anhydrides in N,N-dimethylacetamide" @default.
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- W1997084942 doi "https://doi.org/10.1039/a706743g" @default.
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