One‐ and Two‐Electron Oxidations of Pagodanes and Bissecododecahedradienes: Unusually Persistent Radical Cations

That a radical cation of a quasi saturated hydrocarbon has a half-life of two days at room temperature is extremely unusual. The radical cations generated from 1 and 3 (X  CH2) are identical (4, X  CH2); 4 can be further oxidized to the dication 6 (X  CH2). The reaction 2 → 5 → 7 (X = (CH2)2) can be carried out analogously.