Sulphoxidation reactions

Bohme77 employed excess monoperphthalic acid in diethyl ether to oxidize dibenzyl and benzyl ethyl sulphoxides. Reaction time was 24 h at - 15 to + 10 °C, after which he added potassium iodide and water and titrated the iodine set free with thiosulphate. Dickenson78 oxidized dimethyl sulphoxide in malt, wort or beer with Na2S2Os. In... 

Arylsulphonyl radicals 879 Arylthiomethyl sulphoxides, reactions of 331 / -Arylthiovinyl sulphoxides, synthesis of 345 Aryl unsaturated alkyl sulphones, mass spectra of 137-143... 

Bunnett and Olsen equation 566 Butadienyl sulphones, reactions of 644, 652 Butadienyl sulphoxides reactions of 360 synthesis of 246, 279... 

Cycloheptatrienes, synthesis of 801 Cyclohexadienes 800, 801 Cyclohexanols, synthesis of 838 Cyclopentanones, naturally occurring 321 Cyclopentanone sulphoxides, reactions of 341... 

Dithiolane oxides, synthesis of 241 Dithiolanes, asymmetric oxidation of 291 Divinyl sulphones, reactions of 642, 1021 Divinyl sulphoxides reactions of 349, 352, 353, 359 synthesis of 240 Donor-acceptor capacities 387... 

Phosphorylation 341, 342 Phosphoryl sulphoxides reactions of 333, 825 synthesis of 70, 246, 341, 342 Photochemical oxidation 877, 878 Photoelectron spectroscopy, of... 

Equimolar quantities of benzhydrol and the phosphorane (3a) were also reacted in dimethyl sulphoxide solution. Apart from bis(benzhydryl) ether (18%) and catechol monobenzhydryl ether (39%), a small amount of benzophenone (17%) was obtained. It was shown that, in the absence of phosphorane, benzhydrol is not oxidised to benzophenone by dimethyl sulphoxide. Reaction similar to that outlined in Scheme 1 is a likely possibility. Again, the alcohol is activated by reaction with the phosphorane toward nucleophilic attack, in this case by dimethyl sulphoxide. Significantly, oxidation of alcohols by dimethyl sulphoxide is usually carried out using the Pfitzner-Moffatt reagent (dicyclohexyl carbodiimide and anhydrous phosphoric acid in dimethyl sulphoxide) (13) whereas the reaction using the phosphorane (3a) is carried out under neutral conditions. Unfortunately, however, attempts to improve the yield of benzophenone have hitherto failed. 

In the case of vertebrates, phenothiazines have also been used as antipsychotic drugs for many years, before the beginning of the investigation of their action on a molecular level. Indeed, recently a number of works have appeared on the influence of phenothiazines on the nicotinic synaptic transmission, indicating that the contribution of cytochrome P-450 isoenzymes to N-demethylation and 5-sulphoxidation reactions was involved. The action of phenothiazine antipsychotics on the pre- and post-synaptic neurotransmission was experimentally examined on the tissues and enzymes extracted from the same neuronal tissues. Some phenothiazines were proposed to treat peripheral neuropathy. A new hope might also arise in the search for novel antipsychotic drugs based on phenothiazines to treat Alzheimer s disease and other taupathies, because these new compounds could inhibit tau filament formation. 

Tropone is produced when the tropylium cation is oxidised by dimethyl sulphoxide, reaction proceeding via nucleophilic attack on the cation [69] ... 

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