Iminoiodanes serve as excellent nitrenoid progenitors in the aziridination of olefins and in the C-H amidation of alkanes under transition metal-catalyzed conditions. The methodology for synthesis of the iminoiodanes is, however, very limited and all of the methods reported rely on ligand exchange on iodine of aryliodanes. We report the first example of transimidations yielding sulfonyliminoiodanes, which involves an imido transfer from iminobromane to the iodine atom of iodobenzenes at room temperature under metal-free conditions. Rate dependence on the concentration of iodobenzene suggests a bimolecular nitrenoid transition state, involving a rate-limiting nucleophilic attack of iodobenzene on the negatively charged nitrogen of sulfonyliminobromane. Hammett plot indicates large buildup of positive charge on the iodine of iodobenzenes in the transition state.
