7064-07-5Relevant articles and documents
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Crabbe,P. et al.
, p. 711 - 725 (1971)
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Magtrieve (CrO2) and MnO2 mediated oxidation of aldoximes: Studying the reaction course
Bhosale, Sandeep,Kurhade, Santosh,Vyas, Samir,Palle, Venkata P.,Bhuniya, Debnath
scheme or table, p. 9582 - 9588 (2011/01/03)
Magtrieve (CrO2) and MnO2 mediated oxidation of aldoximes to nitrile oxides were studied in details. In presence of external radical source, TEMPO, these reagents did not furnish nitrile oxides, instead favoured deoximation to aldehydes. A common trend of deoximation was established from electronically tuned aldoximes, which is: aliphatic>aromatic> aldoximes with strong electron-withdrawing group, though the extent of deoximation was less in case of CrO2. Above effects were not observed with chloramine-T and diacetoxyiodobenzene, reagents known to produce nitrile oxides via hydroximoyl halide or equivalent ionic intermediates. A putative reaction mechanism is proposed for MO2 (M=Cr, Mn) mediated oxidation of aldoximes through formation of a nitroso-oxime tautomeric pair. Formation of nitrile oxide is possibly occurred from the oxime tautomer via a σ-type iminoxy radical intermediate. The deoximation process, dominating in presence of external radical environment, is explained following decomposition of the nitroso tautomer.
Generation of nitrile oxides from oxime derivatives by the oxidation with ammonium hexanitratocerate(IV)
Arai, Noriyoshi,Iwakoshi, Mitsuhiko,Tanabe, Katsuhiko,Narasaka, Koichi
, p. 2277 - 2285 (2007/10/03)
Aromatic and aliphatic nitrile oxides are generated by the oxidation of α-hydroxyimino carboxylic acid with ammonium hexanitratocerate(IV). They react with olefinic and acetylenic dipolarophiles to give the corresponding cycloaddition products in good yield. The oxidation of α-oxo aldoximes also affords α-oxo carbonitrile oxides.