Abstract
The electroreductive coupling of activated olefins and 1–3 dibromide reported in a previous paper leads to a cyclic product when the reaction is carried out in an undivided cell in NMP and in the presence of a sacrificial aluminum anode, but not in a divided cell A mechanistic study has been made to explain the discrepancy between the two methods. We report here that in the undivided cell and in the presence of anodically generated aluminum ions the electroreduction of activated olefins mainly lead to a dianion, while a radical anion is the main reactive species under the other experimental conditions.
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Unpblished.
We do not ignore that finding the ring-open product does not necessarily infer that the mechanssm involves the cyclopropylmethyl radical as the key intermediate (see Ref. 17). But assuming a non-radical mechanism with styrene would make difficult the understanding of the behaviour of the reagent mixture containing either 2 or 3 in the undivided cell when the reaction was carried out in the presence of aluminum ions.
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Lachaise, I., Lu, Y.W., Nédélec, J.Y. et al. Intermediate and reaction mechanism of the electroreductive coupling of activated olefins and alkyl dihalides using the sacrificial anode process. Res Chem Intermed 15, 253–260 (1991). https://doi.org/10.1163/156856791X00363
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DOI: https://doi.org/10.1163/156856791X00363