Oxidation of arylamidoximes by various chemical and biomimetic systems: comparison with their oxidations by hemeproteins

Citation
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
ISSN journal
13871609 → ACNP
Volume
3
Issue
10
Year of publication
2000
Pages
785 - 792
Database
ISI
SICI code
1387-1609(200010)3:10<785:OOABVC>2.0.ZU;2-8
Abstract
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.