Abstract
The oxidation of vic-dioximes to furoxans by copper(II) perchlorate in acetonitrile as the oxidant has been discussed. This method was found to be applicable for a broad range of vic-dioximes. Copper complexes of 1,10-phenanthroline derived furoxans were isolated by oxidation of the corresponding copper(II) complexes of 1,10-phenanthroline based dioximes. In exploring the mechanism of copper(II)-mediated oxidative cyclization of vic-dioxime, a transient blue species was observed in the reaction pathway. Based on the spectroscopic signatures and reactivity patterns, the intermediate was proposed to be a dioximate-copper(II)-dinitrosoalkene complex. These results along with the role of metal ion and solvent in the oxidative transformation reaction are discussed in this review.
Copper(II) salts in acetonitrile oxidize vic-dioximes to furoxans gave high yields under ambient conditions. A dioximate-copper(II)-dinitrosoalkene intermediate is implicated in the reaction pathway.
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This research was financially supported by the Department of Science and Technology (DST), Government of India.
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DAS, O., PAINE, T.K. Mechanistic studies of copper(II)-mediated oxidation of vic-dioxime to furoxan. J Chem Sci 124, 1269–1273 (2012). https://doi.org/10.1007/s12039-012-0341-2
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DOI: https://doi.org/10.1007/s12039-012-0341-2