Phenyliodonium imide

Several phenyliodonium imides 465 derived from heteroarenesulfonylamides have been synthesized from (diacetoxyiodo)benzene and the respective amides 464 (Scheme 2.134) [630], Imides 465 can be used as sources of the corresponding heterocycle-containing nitrenes in the copper-catalyzed aziridination and sulfimidization reactions. 

A single-crystal X-ray analysis of orf/to-sulfonyl substituted phenyliodonium imide 467 showed a structure of loosely associated centrosymmetric dimers with a long-range intramolecular I-N and I-O distance of more than 3.0 A, quite unlike the infinite polymeric chains adopted in the solid state for PhINTs [100]. One of the sulfonyl oxygen atoms forms a short intramolecular T--0 secondary bond to the iodine atom with a bond length of 2.667 A. Because of the non-polymeric structure, imide 467 has excellent solubility in common organic solvents. 

Under the same conditions, arylsulfonamides are converted to phenyliodonium imides or iminoaryl-A -iodanes. 

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