SINGLE-ELECTRONIC CLEAVAGE OF A CARBON-SULFUR BOND IN THE CATHODIC REDUCTION OF 2,3-BIS(PHENYLSULPHONYL)-1,4-DIMETHYLBENZENE IN DIMETHYL SULPHOXIDE

Article abstract of DOI:10.1039/P29840000951

2,3-Bis(phenylsulphonyl)-1,4-dimethylbenzene, dissolved in dimethyl sulphoxide, undergoes a one-electron single reduction wave at -1,6 V respect to Ag-Ag(1+)(0.01M).The reduction was studied by differential pulse polarography, cyclic voltametry, 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.

Full text of DOI:10.1039/P29840000951

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