A reaction of silole anion {[MeSiC4Ph4]−•[Li+ or Na+] (1) with anhydrous ferrous chloride (FeCl2) in THF (tetrahydrofuran) gives 1,1′-bis(1-methyl-2,3,4,5-tetraphenyl-1-silacyclopentadienyl) [Ph4C4Si(Me)-(Me)SiC4Ph4] (2) with precipitation of iron metal in high yield. Silole dianion {[SiC4Ph4]2−•2[Li+] (3) is added to anhydrous cupric chloride (CuCl2) in THF at −78 °C, then the dark red solution changes into a greenish solution. From the solution, a green solid is isolated, and stirring it in

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... luene at room temperature provides quantitatively 1,1′-bis(1-chloro-2,3,4,5-tetraphenyl-1-silacyclopentadienyl) [Ph4C4Si(Cl)-(Cl)SiC4Ph4] (4) with precipitation of copper metal in toluene. The green solid is suggested to be 1,1′-bissilolyl bisradical [Ph4C4Si-SiC4Ph4]2• (8), and lithium cuprous chloride salts {[Li2CuICl2]+•[CuICl2]−}. Both reactions are initiated by single-electron transfer (SET) from the electron-rich anionic silole substrates (1 and 3) to iron(II) and copper(II).