We report a “threading followed by shrinking” approach toward rotaxane synthesis using an “oxygen-deficient” macrocycle containing two arylmethyl sulfone units and the dumbbell-shaped salt bis(3,5-dimethylbenzyl)ammonium tetrakis(3,5-trifluoromethylphenyl)borate as the host and guest components, respectively. Extruding SO2 from both of the arylmethyl sulfone motifs of the corresponding [2]pseudorotaxane resulted in a [2]rotaxane that was sufficiently stable to maintain its molecular integrity in CD3SOCD3 at 393 K for at least 5 h.