Abstract The sulfonation of cyclopropylbenzene (1a) and cyclopropyl phenyl ketone (5) with sulfur trioxide in both nitromethane and 1, 4-dioxane as solvent has been studied. Sulfonation of cyclopropylbenzene (1a) with up to 2.0 mol-equiv. of SO3 in dioxane leads to the initial formation of 3-phenyl-1, 3-propanesultone (2a) which product subsequently slowly isomerizes to 3-phenyl-2-propene-1-sulfonic acid (4a). Sulfonation of 1a with 4.0 mol- ...