Sulphonyl sulphoxides alkylation

Sulphonyl phosphates, reactions of 638 Sulphonyl radicals 215 cyclization of 1099 ESR spectra of 1090-1093 formation of 1094-1098 structure of 1090-1094 thermodynamic data for 1094 Sulphonyl sulphenes 196 Sulphonyl sulphoxides alkylation of 311 synthesis of 262... 

The use of chlorine as an oxidizing agent for the conversion of sulphoxides into sulphones is completely unsuccessful under anhydrous conditions. In aqueous solutions, the sulphone is formed but this is usually part of a complex mixture of chlorinated sulphoxides, chlorinated sulphones and sulphonyl chlorides89, so that the reaction is usually not very useful as a preparative method for alkyl sulphones. Dimethyl sulphone has however been obtained in 70% yield in one isolated case90. In methanol solution dibenzyl sulphoxide is cleanly oxidized to dibenzyl sulphone and benzyl sulphonyl chloride in reasonable overall yield91. 

In contrast to the problems encountered on photolysis of alkyl- and aryl-sulphonyl azides, we have found that ferrocenylsulphonyl azide 74 is smoothly decomposed by 3500 A light in cyclohexane or in benzene to give ferrocene 15, ferrocenylsulphonamide 16 and the novel bridged [2]ferrocenophanethiazine 1,1-dioxide 17 24>. The yield of 17 varied with the nature of the solvent, being 13.3% in cyclohexane, 67% in benzene, and zero in dimethyl sulphoxide or DMSO/benzene 25>. 

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