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- W4247732940 abstract "The reduction of several aromatic carbonyl compounds in ethanolic alkaline media has been investigated. According to the structure of the carbonyl compound and the acidity of the medium, either two one-electron waves or one two-electron wave are observed. For the two one-electron wave system, the first one-electron wave may correspond either to a pinacol or to a stable anion radical. For the dimerization mechanism, three possibilities must be considered: purely radical, ionic radical and purely ionic coupling. From kinetic studies using mainly linear sweep voltammetry, it is concluded that the dimerization mechanism is composed of a rate determining coupling between a neutral ketyl radical and an anion ketyl radical, preceded by a fast and equilibrated protonation and eventually followed by neutralization of the pinacolate. The question is then discussed as to whether the two-electron wave in the reduction of aromatic carbonyl compounds reflects an e.c.e. mechanism, as generally assumed, or the occurrence of a disproportionation process, and whether the reduction mechanism changes from one process to the other according to the structure of the carbonyl compound and the composition of the medium. Kinetic studies using linear sweep voltammetry show the direct interference of disproportionation in the reduction process as a rate determining step in a large number of cases. The conclusion to be drawn from this study of the two-electron wave is that acid catalyzed electron transfer disproportionation of the initial electrode product is the most common reaction path in the reduction of aromatic carbonyl compounds in alkaline medium." @default.
- W4247732940 created "2022-05-12" @default.
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- W4247732940 date "1971-12-01" @default.
- W4247732940 modified "2023-10-14" @default.
- W4247732940 title "Dimerization, disproportionation and E.C.E. mechanisms in the reduction of aromatic carbonyl compounds in alkaline media" @default.
- W4247732940 doi "https://doi.org/10.1016/0368-1874(71)80049-7" @default.
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