Synthesis, structure, and chemoselective reactivity of N-(2-iodylphenyl) acylamides: Hypervalent iodine reagents bearing a pseudo-six-membered ring.scaffold

A pseudo-benziodoxazine structure with intramolecular secondary I⋯O bonding, as shown by X-ray analysis, is seen in a series of N-(2-iodylphenyl) acylamides prepared from 2-iodoaniline (see scheme). These compounds contain a six-membered pseudocyclic scaffold about an iodine(v) center and are able to oxidize either alcohols or sulfides, with the reactivity depending largely on the substitution pattern on the amide group adjacent to the iodyl moiety. (Chemical Equation Presented).