Electrochemical oxidation oximes

Usually, electrochemical oxidative hydrolysis of ketoximes affords the corresponding ketones. Hence, 2-octanone (equation 13) and acetophenone were obtained from the corresponding ketoximes in 90% and 97% yields, respectively. However, camphor oxime was transformed into the ring-cleaved nitrile (equation 14). ... 

Electrochemical oxidation of aldoximes using halide ions as mediators afforded the corresponding nitrile oxides in the anode compartment, which were simultaneously reduced to nitriles by cathodic reduction (equation 15). Sodium chloride affords the best result among the supporting electrolytes (Cl > Br > 1 > C104 > TsO ). Accordingly, the electrochemical reaction of oximes carried out in the presence of dipolephiles yielded isooxazolines (equation 16). 

Electrochemical oxidation of phenol substituted by a side chain containing an oxime group afforded a spiro-isoxazole in a quantitative yield (equation 18) . 

Cleavage of oximes to the parent carbonyl compound may be performed under mild conditions by anodic oxidation in CH3CN/H2O [123]. Thus, anodic oxidation of 4-sub-stituted acetophenone oximes in wet acetonitrile furnishes the corresponding acetophenones in high yields, while the oxidation of benzaldoximes is unselective [124] [Eq. (18)]. By indirect electrochemical oxidation using the Mn(II)/Mn(III) mediator system in the... 

Electrochemical reduction of benzylic nitro compounds (27) in an ethanolic aqueous acetic acid buffer (35 65) affords a mixture of the corresponding oxime and hydroxylamine (equation 6)48. The hydroxylamine can subsequently be oxidized back to the oxime (28) (via the intermediate nitroso compound) conversions as high as 90% can be obtained. 

The mixed amine-imine-oxime ligands HL (415) and HT (416) have been found to be effective in stabilizing nickel(IV). The complexes Ni(L)(C104)2 (418) and Ni(T)2(C104)2 (419) can be obtained by oxidation of solutions of the parent nickel(II) complexes with various oxidizing agents (I Os, SiOl", Pb02, Fe(bipy) ) or electrochemically. ... 

An electrochemically induced change of spherical micelles to larger aggregates was observed for coumarin-containing block copolymers [294]. Electrochemical addressability was also found for ferrocene-based micelles of block copolymers, which can undergo conjugation with hydroxylamines in terms of an oxime function [186]. After conjugation micelles are formed, whose size can be manipulated by the oxidation state of the ferrocene units (here only reported by chemical redox). 

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