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The oxidative [4 + 2] reaction of o-phenylenediamine-derived disulfonamides with fullerene C₆₀ and C₇₀ is reported, in which electron-deficient reactants showed high reactivity. The reaction of C₇₀ exhibited unusual regioselectivity, yielding a [5,6]-adduct as the major product, which was characterized by ¹H, ¹³C NMR and single-crystal X-ray diffraction. DFT calculations revealed the reaction is an inverse-electron-demand Diels–Alder (IEDDA) reaction, and the [5,6]-adduct of C₇₀ is a kinetic product.