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Here we show that the sp‐hybridized nitrogen cation is strongly stabilized by a peri‐iodine substituent in the tetralone system. The cation is captured by anionic species such as CF3CO2−, affording hypervalent iodine(III) compounds with a short nitrogen‐iodine (N−I) bond, in which the cation serves as a Lewis acid. Notably, the O−I bond of the O‐trifluoroacetate or O‐acetate is intrinsically weaker...