Magtrieve™ (CrO2) and MnO2 mediated oxidation of aldoximes: studying the reaction course
作者： Sandeep Bhosale , Santosh Kurhade , Samir Vyas , Venkata P. Palle , Debnath Bhuniya
DOI: 10.1016/J.TET.2010.10.029
关键词:
摘要: Abstract Magtrieve™ (CrO2) and MnO2 mediated oxidation of aldoximes to nitrile oxides were studied in details. In presence external radical source, TEMPO, these reagents did not furnish oxides, instead favoured deoximation aldehydes. A common trend was established from electronically tuned aldoximes, which is: aliphatic>aromatic>aldoximes with strong electron-withdrawing group, though the extent less case CrO2. Above effects observed chloramine-T diacetoxyiodobenzene, known produce via hydroximoyl halide or equivalent ionic intermediates. putative reaction mechanism is proposed for MO2 (M=Cr, Mn) through formation a nitroso-oxime tautomeric pair. Formation oxide possibly occurred oxime tautomer σ-type iminoxy intermediate. The process, dominating environment, explained following decomposition nitroso tautomer.
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