Abstract
The regularities of electroreduction of 5-substituted isoxazoles are studied by examining their cyclopropyl and phenyl derivatives. It is found that this process proceeds on a steel electrode according to the mechanism of direct cathodic deprotonation and is accompanied by the removal of a proton from the 3rd position of the isoxazole ring with the formation of a corresponding carbanion, which is readily isomerized to enolate anion of an open type. The same mechanism is realized also in the electroreduction of 5-substituted isoxazoles on cathodes with a high overpotential of hydrogen evolution (C, Hg). An alternative process, namely, an indirect cathodic deprotonation of 5-substituted isoxazoles, can be realized with the use of MeOH or t-BuOH as the prebases.
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Original Russian Text © V.A. Petrosyan, S.V. Neverov, V.L. Sigacheva, B.V. Lyalin, 2007, published in Elektrokhimiya, 2007, Vol. 43, No. 7, pp. 786–793.
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Petrosyan, V.A., Neverov, S.V., Sigacheva, V.L. et al. Cathodic deprotonation of 5-substituted isoxazoles. Russ J Electrochem 43, 750–757 (2007). https://doi.org/10.1134/S1023193507070026
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DOI: https://doi.org/10.1134/S1023193507070026