In strong Brønsted acids (CF₃SO₃H, FSO₃H, D₂SO₄), (arysulfonyl)allenes (ArSO₂-CR¹=C=CR²R³) and (arylsulfinyl)allenes (ArSO-CR¹=C=CR²R³) undergo cyclization into the corresponding stable 1,2-oxathiolium ions, which were studied by means of NMR and DFT calculations. Quenching of solutions of these cations with low nucleophilic media, aqueous HCl, leads to their deprotonation with a stereoselective formation of (arysulfonyl)butadienes (for instance, ArSO₂-CR¹=C-C(Me)=CH₂, for R² = R³ = Me, yields of 87-98%). Reactions of (arysulfonyl)allenes in the system TfOH (0.1 equiv)-HFIP (hexafluoropropan-2-ol) followed by hydrolysis give rise to allyl alcohols (ArSO₂-CR¹=CH-C(OH)R²R³, yields of 78-99%). Reflux of solutions of (arysulfonyl)allenes in the presence of TfOH (1 equiv) in 1,2-dichlorobenzene leads to the cyclization into thiochromene 1,1-diox-ides in high yields. Under the action of TfOH or AlX₃ (X = Cl, Br) followed by hydrolysis of reaction mixtures, (arylsulfinyl)allenes give allyl alcohols (ArSO₂-CR¹=CH-C(OH)R²R³). Plausible reaction mechanisms have been proposed for all studied reactions.