- Reductive-alkylation and aromatic coupling reactions of 1,4-benzoquinone derivatives promoted by ethylaluminum dichloride
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Reactions of several substituted 1,4-benzoquinones with ethylaluminum dichloride in dichloromethane were studied. It was found that some quinones undergo a new radical aromatic coupling under these conditions, while others undergo a 1,6-reductive O-alkylation.
- Ferreira, Vitor F.,Schmitz, Francis J.
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- ELECTRON-TRANSFER PROCESSES: MECHANISMS OF OXIDATION OF ETHERS AND ESTERS BY SILVER-CATALYZED PEROXYDISULPHATE
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Nucleophilic carbon-centred radicals, generated from the oxidation of diethyl ether, ethyl acetate, propyl acetate, ethyl propionate, diethyl oxalate and 2-phenylethyl acetate by silver-catalyzed decomposition of peroxydisulphate, have been trapped, mostly by naphthoquinone and in a few cases by protonated quinoline. Characterization of the intermediate radicals allows the rationalization of the mechanism of these oxidations, which are likely to occur through an initial electron-transfer step by Ag(II).
- Minisci, Francesco,Coppa, Fausta,Fontana, Francesca,Zhao, Lihua
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p. 613 - 616
(2007/10/02)
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