Electrochemical oxidation of 1,5-dithiacyclooctane (DTCO), 1a, involves a two-electron reversible process. The two electrons are removed stepwise but a single oxidation peak is observed because the cation radical is oxidized more readily than DTCO itself! Similarly, the electrochemical oxidation of 1,5-diselenocyclooctane (DSeCO), 2a, is also reversible. We have now found 3a or ditellurocyclooctane (DTeCO), 3a, also undergoes a reversible, two-electron oxidation. However, cyclic voltammetric studies with silicon and tin substituted in the aforementioned chalcogen-chalcogen mesocycles show irreversible oxidations. Unlike 1b-e and 2b-c silatellurium compounds 3b and 3c undergo reversible oxidation which have been fitted by simulations. The chemical basis for these results will be presented.