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Synthesis, Structure, and Chemoselective Reactivity of N ‐(2‐Iodylphenyl)acylamides: Hypervalent Iodine Reagents Bearing a Pseudo‐Six‐Membered Ring Scaffold
Author(s) -
Ladziata Uladzimir,
Koposov Alexey Y.,
Lo Ka Y.,
Willging Jeff,
Nemykin Victor N.,
Zhdankin Viktor V.
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200502707
Subject(s) - hypervalent molecule , moiety , intramolecular force , reactivity (psychology) , chemistry , ring (chemistry) , iodine , reagent , amide , scaffold , combinatorial chemistry , stereochemistry , organic chemistry , computer science , database , medicine , alternative medicine , pathology
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.