The effect of the nature of the solvent (DMF, DMSO, CH3CN, N-methylpyrrolidinone, THF) and supporting electrolyte (Bu4NBr, Et4NBr, Et4NClO4,Me4NBr, LiBF4, NaBF4, and KBF4) on the electrochemical activation and carboxylation of fluorine-containing aromatic imines by the action of CO2 was studied for the case of p-and m-fluorobenzylideneaniline. It was shown that factors promoting the formation of intimate ion pairs between the radical-anions of the imines – the initial products of the processes in the electrochemical activation of the imines – and the cations of the supporting electrolyte (decrease of the polarity of the medium and decrease of the radius of the cation in the supporting electrolyte) significantly reduce the effectiveness of electrochemical carboxylation right down to its complete cessation.
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Teoreticheskaya i Éksperimental’naya Khimiya, Vol. 46, No. 1, pp. 8-13, January-February, 2010.
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Titov, V.E., Bondarenko, V.N., Koshechko, V.G. et al. Effect of the nature of the solvent and the supporting electrolyte on the electrochemically activated insertion of CO2 into fluorine-containing aromatic imines with the production of amino acids. Theor Exp Chem 46, 8–13 (2010). https://doi.org/10.1007/s11237-010-9113-6
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DOI: https://doi.org/10.1007/s11237-010-9113-6