2,3-Bis(phenylsulphonyl)-1,4-dimethylbenzene, dissolved in dimethyl sulphoxide, undergoes a one-electron single reduction wave at -1.6 V with respect to Ag-Ag<sup>+</sup> (0.01 M). The reduction was studied by differential pulse polarography, cyclic voltammetry, and controlled-potential electrolysis. Fast chemical steps follow the initial reduction and the isolated products are 1,4-dimethyldibenzothiophene 5,5-dioxide and 1,4-dimethyl-2-(phenylsulphonyl) benzene. In some experiments small percentages of 5a,9a-dihydro-1,4- dimethyldibenzothiophene 5,5-dioxide are also obtained. The results argue in support of the electron-transfer mechanism previously proposed for the photoinduced reactions of the same substrate with sodium arenethiolates in dimethyl sulphoxide.

Single-electronic cleavage of a carbon-sulphur bond in the cathodic reduction of 2,3-bis(phenylsulphonyl)-1,4-dimethylbenzene in dimethyl sulphoxide

CAPODAGLIO, Gabriele
1984-01-01

Abstract

2,3-Bis(phenylsulphonyl)-1,4-dimethylbenzene, dissolved in dimethyl sulphoxide, undergoes a one-electron single reduction wave at -1.6 V with respect to Ag-Ag+ (0.01 M). The reduction was studied by differential pulse polarography, cyclic voltammetry, and controlled-potential electrolysis. Fast chemical steps follow the initial reduction and the isolated products are 1,4-dimethyldibenzothiophene 5,5-dioxide and 1,4-dimethyl-2-(phenylsulphonyl) benzene. In some experiments small percentages of 5a,9a-dihydro-1,4- dimethyldibenzothiophene 5,5-dioxide are also obtained. The results argue in support of the electron-transfer mechanism previously proposed for the photoinduced reactions of the same substrate with sodium arenethiolates in dimethyl sulphoxide.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10278/34931
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