ChemInform Abstract: Some Peculiarities of the Preparative Electroreduction of Allyldimethylsulfonium Salts.

Abstract

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Electrode reactions and electroanalysis of organomercury compounds

“…The preparative ER of allyl dimethyl sulfonium salts was also complicated by the subsequent slow chemical reactions resulting in organomercury intermediates that could not be detected under polarographic conditions. 193 Besides the duration of the studied process, the state of the mercury electrode surface often proved to be of fundamental importance for the OMC formation. For example, voltammograms of iodo-and bromobenzenes, 128 lysozyme, 243 glutathione, 244 thiadiazoline derivative of spiroadamantane 245,246 and several other compounds, recorded on fresh mercury surface, on the one hand, and during repeated scans, on the other hand, dramatically differed from one another, the latter demonstrating new cathodic and anodic peaks.…”

“…195 In water ± ethanol solutions, its yield was virtually quantitative, which allowed electrolysis to be recommended as a convenient method for the removal of a sulfonyl protecting group from position 2 of the pyridine ring. It was established 192,193 that preparative two-step ER of allyl methyl sulfonium perchlorates at a mercury cathode in DMF was accompanied by the OMC formation and subsequent slow chemical transformations. Based on the proposed mechanism, the methods of preparation of a-isoprenoids were proposed.…”