Oxidation of the macrocyclic thioether sulfones (S phi SO(2)phi)(n) (phi = 1,4-phenylene; n = 2 or 3) affords sulfone-linked paracyclophanes (phi SO2)(4) and (phi SO2)(6); single crystal X-ray analysis reveals the tetramer, (phi SO2)(4), to be a near-perfect square box, whilst the hexamer, (phi SO2)(6), adopts a much more irregular conformation; exhaustive oxidation of (S phi SO(2)phi)(4), leads not to the expected octamer, (phi SO2)(8), but to the heptasulfone sulfoxide [(phi SO2)(7)(phi SO)].