The electrochemical oxidation of 1,1-bis(trimethylsilyl)-2,3,4,5-tetraphenyl-1-silacyclopentadiene has been investigated under different conditions. The effect of electrolyte, electrode material and atmosphere on the outcome of its electrochemical oxidation are discussed. Under all conditions studied, the silole derivative studied undergoes ring-opening, sometimes with the extrusion of the silicon moiety.