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Electrochemical reduction mechanism of sulfilimines: S, S-diphenyl-N-p- nitrobenzenesulfonylsulfilimine

✍ Scribed by Luciana Griggio

Publisher
Elsevier Science
Year
1982
Tongue
English
Weight
427 KB
Volume
27
Category
Article
ISSN
0013-4686

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✦ Synopsis

The electrochemical behaviour of S, S-diphenyl-N-p-nitrobenzenesulfonylsulfilimine has been investigated in formally aprotic medium (DMF). The compound presents four polarographic reduction waves and four cathodic peaks in potential sweep voltammetry. The first wave corresponds to a reversible one-electron transfer leading to the radical anion of the compound, as revealed by epr spectrometry. The radical decays through a disproportionation process yielding, besides the parent compound, nitrobenzenesulfonamide anion and diphenylsulfide as main products, the latter compounds resulting from a fast cleavage of the sulfiliminic S N bond in the dianion of the sulfilimine. The second reduction step corresponds to a two-electron transfer yielding directly the sulfilimine dianion, which undergoes a cleavage as previously indicated The third reduction wave is atlributable Lo the reduction of cleavage products of the dianion. The third and fourth reduction waves are attributable to the reduction of cleavage products of the sulfilimine.

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