Abstract
AbstractSulfonation of anthracene‐9‐d with sulfur trioxide‐dioxane in dioxane as solvent at 40° leads to 31 ± 2% α‐, 8 ± 2% β‐ and 61 ± 2% meso‐substitution. The substitution at the meso‐position proceeds with a maximal substrate kinetic isotope effect of hydrogen ‐ kH/kD = 6.8 with 5.6 and 8.6 as limiting values ‐ indicating that the proton removal from the σ‐complex is rate‐limiting.From the data for anthracene‐9‐d it was calculated that the sulfonation of C14H10 leads to 21 ± 3% 1‐, 6 ± 2% 2‐ and 73 ± 5% 9‐substitution.
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