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The mechanism of sulfonation in oleum proposed by Brand et af. -stepwise attachment of so3 and H+ to the substrate, followed by the loss of the proton from the benzene ring -is shown to be inconsistent with the substrate isotope effects reported by these authors. The sulfonation kinetics of p-di-, 1,2,3,4-tetra-, and penta-fluorobenzene in 97-109 % sulfuric acid are discussed in terms of an extrapolation of the mechanism proposed recently for aqueous sulfuric acid. In weak oleum -below 104% sulfuric acid -the rate-limiting step is \ IntroductionThe kinetics of aromatic sulfonation in oleum have been studied by Brand et al. l-3 and Cerfontain 475. The sulfonation rates of trimethylphenylammonium ions 1~2 and of the un-ionized forms of nitrobenzenes 1,

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