Electrochemical oxidation of cyclooctatetraene in the presence of allyltrimethylsilane. Anodic trialkylation with bicyclization

Anodic oxidation of cyclooctatetraene (COT) was carried out in acetonitrile containing excess allyltrimethylsilane. Under these conditions COT is oxidized preferentially to afford the COT cation radical, which then undergoes nucleophilic attack by the silane followed by further anodic oxidation. The process results in a substance in which the original eight carbons of COT are highly differentiated by the addition of three allyl groups and the formation of two new rings.