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. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z502707_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.