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- W2015874750 abstract "The electrochemical reduction of aromatic aldehydes (ArCHO) such as 2-naphthaldehyde (1), 4-dimethylaminobenzaldehyde (2), 3-methoxybenzaldehyde (3) and 2-pyrrole carboxaldehyde (4) in N,N-dimethylformamide with tetrabutylammonium hexafluorophosphate as supporting electrolyte, under an argon atmosphere and in the presence of protons donors (AH2) such as fluorene (FlH2) or indene (InH2), gives products such as (ArCH2A) and/or [ArCH(AH)2] (AH=FlH or InH). Three consecutive chain reactions are initiated by proton abstraction from fluorene or indene by a base electrogenerated by the reduction of ArCHO. The propagation steps of the first chain reaction involves addition of AH- to ArCHO and protonation of the resulting alcoholate with regeneration of AH- to give the carbinol ArCH(OH)AH. The second chain reaction is the base-catalyzed dehydration of ArCH(OH)AH to ArCH2A. The third is the addition of AH- to ArCH2A, giving ArCH(AH)2 with regeneration of AH-. Re′actions en chaine induites e′lectrochimiquement. Re′actions d'alde′hydes aromatiques induites par des bases e′lectroge′ne′re′es. La re′duction e′lectrochimique d'alde′hydes aromatiques (ArCHO) tels que le 2-naphtalde′hydes (1), le 4-dime′thylaminobenzalde′hyde (2), le 3-me′thoxybenzalde′hyde (3) et le 2-pyrrolecarboxaldehyde (4) en pre′sence d'hexafluorophosphate de te′trabutylammonium comme e′lectrolyte support sous l'influence de donneurs de protons AH2 tels que le fluorene (FlH2) ou l'indene (InH2) conduit aux compose′s ArCH2A et (ou) ArCH(AH)2 (AH=FlH ou InH). Trois re′actions en chaine conse′cutives sont initie′es par abstraction d'un proton de AH2 par la base e′lectroge′ne′re′e par re′duction de ArCHO. L'e′tape de propagation de la premiere re′action en chaine correspond a l'addition de l'anion AH- sur l'alde′hyde ArCHO suivie de la protonation de l'alcoolate re′sultant par AH2 pour conduire a l'alcool ArCH(OH)AH avec re′ge′ne′ration de AH-. La seconde re′action en chaine correspond a la de′shydratation de ArCH(OH)AH en ArCH2A sous l'influence de la base AH-; enfin la formation de ArCH(AH)2 s'effectue par addition de AH- sur ArCH2A suivie d'une protonation par AH2." @default.
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- W2015874750 date "1999-01-01" @default.
- W2015874750 modified "2023-09-26" @default.
- W2015874750 title "Electrochemically induced chain reactions. Reactions of aromatic aldehydes induced by electrogenerated bases" @default.
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- W2015874750 doi "https://doi.org/10.1039/a904036f" @default.
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