101ChemInform Abstract The thermal decomposition of cumene hydroperoxide (I) in the phenyl cycloalkanes (II) as solvents is studied by product analysis (GC) in order to clear whether the oxidation proceeds by free radicals or by an SE2 mechanism and whether ring size effects are operating. Indeed, a free-radical mechanism is proven to work as well as is a ring-size effect being in accord with the I-strain concept. The decomposition of both tBuOOH and cumene hydroperoxide (I) in phenyl cyclopropane is studied as well.