S. Vadon-le Goff et al., Oxidation of arylamidoximes by various chemical and biomimetic systems: comparison with their oxidations by hemeproteins, CR AC S IIC, 3(10), 2000, pp. 785-792
Citations number
27
Categorie Soggetti
Chemistry
Journal title
COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II FASCICULE C-CHIMIE
Oxidation of 4-chlorobenzamidoxime by various chemical systems leads to the
corresponding amide and nitrile, and to three dimeric compounds in greatly
variable amounts as a function of the oxidizing agent. Monoelectronic oxid
ants, such as Pb(OAc)(4) and Ag2CO3, selectively led to 4-chlorobenzonitril
e, whereas hydroperoxides such as H2O2 and tBuOOH only led to 4-chlorobenza
mide. Other oxidants like m-chloroperbenzoic acid and Br-2 gave more comple
x mixtures. Introduction of an iron-porphyrin catalyst in the oxidation per
formed by tBuOOH and m-chloroperbenzoic acid resulted in a spectacular incr
ease of the formation of 4-chlorobenzonitrile. These results suggest that h
igh-valent porphyrin iron-ore species preferentially oxidize arylamidoximes
in a manner similar to monoelectronic oxidants. (C) 2000 Academie des Scie
nces/Editions scientifiques et medicales Elsevier SAS.