Radical ions, 51. Oxidative Rearrangement of Diphenyl Disulfides to Thianthrenes

para ‐Substituted diphenyl disulfides 1 – 5 with low gas phase ionization energies of about 8 eV react with AlCl 3 in CH 2 Cl 2 to form‐radical cations of the corresponding thianthrenes (Table 2, Figure 2). Warming of these solutions produced a second ESR signal which is attributed to a benzodithiete radical cation (Table 2, Figure 3). This is possibly the reactive intermediate in the S 8 or S 2 Cl 2 catalyzed Friedel‐Crafts chlorination of benzene.