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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...
Anodic oxidation of 1,2-,5,6-bis[trimethylene]cyclooctaetraene in methanol affords as the major product a substance formed by a complex sequence of carbon–carbon bond cleavages and concomitant aromatization.
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