Electrochemical behaviour of heterocyclic amine derivatives in media of controlled proton availability: Part II. Reduction mechanism and electron spin resonance study of 2-phenyl 4-substituted quinoline 1-oxides in DMF |
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Authors: | R Andruzzi A Trazza L Greci L Marchetti |
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Institution: | 1. Istituto di Chimica della Facoltà di Ingegneria dell''Università, Via del Castro Laurenziano, 7-00161 Rome, Italy;2. Centro di Studio per la Elettrochimica e la Chimica Fisica delle interfasi del C.N.R., Via del Castro Laurenziano, 7-00161 Rome, Italy |
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Abstract: | The electroreduction of some 4-substituted 2-phenylquinoline 1-oxides in dimethylformamide with and without a protonating agent was studied by dc and ac phase selective polarography, cyclic voltammetry, controlled-potential coulometry, ESR and UV spectrometry.In an aprotic medium the 1-oxides studied exhibit three or four subsequent steps. In every case the first is a reversible one-electron transfer producing a stable anion radical characterized by the ESR spectra. Potential sweep voltammetry give evidence of a chemical reaction following the second electron transfer producing the corresponding free bases, which are also electroactive at the same potentials.In a protic medium two subsequent bi-electronic (or only one tetraelectronic step) can be observed, the corresponding free bases and then 1,4-dihydroquinolines (or directly 1,4-dihydroquinolines) being the final reduction products.According to the experimental evidence a multistep scheme is suggested in which the role played by the substituents in determining the electroreduction pattern is considered. |
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Keywords: | To whom correspondence should be addressed |
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