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Titolo:
An electrochemical aromatic chlorination, comparison with electrophilic reaction
Autore:
Appelbaum, L; Danovich, D; Lazanes, G; Michman, M; Oron, M;
Indirizzi:
Hebrew Univ Jerusalem, Dept Organ Chem, IL-91904 Jerusalem, Israel Hebrew Univ Jerusalem Jerusalem Israel IL-91904 -91904 Jerusalem, Israel Hebrew Univ Jerusalem, Lise Meitner Minerva Computat Ctr, IL-91904 Jerusalem, Israel Hebrew Univ Jerusalem Jerusalem Israel IL-91904 -91904 Jerusalem, Israel
Titolo Testata:
JOURNAL OF ELECTROANALYTICAL CHEMISTRY
fascicolo: 1, volume: 499, anno: 2001,
pagine: 39 - 47
Fonte:
ISI
Lingua:
ENG
Keywords:
anodic chlorination; aromatic ethers; electro-chlorination;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
24
Recensione:
Indirizzi per estratti:
Indirizzo: Michman, M Hebrew Univ Jerusalem, Dept Organ Chem, IL-91904 Jerusalem, Israel Hebrew Univ Jerusalem Jerusalem Israel IL-91904 salem, Israel
Citazione:
L. Appelbaum et al., "An electrochemical aromatic chlorination, comparison with electrophilic reaction", J ELEC CHEM, 499(1), 2001, pp. 39-47

Abstract

The electrophilic and the anodic chlorination of 1,4-dimethoxy-2-tert-butylbenzene appear to involve different mechanistic pathways. The electrophilic chlorination of 1,4-dimethoxy-2-tert-butylbenzene requires Lewis acid catalysts when carried out in CCl4 but not in CH3CN. It yields 1,4-dimethoxy-2-tert-butyl-5-chlorobenzene as the primary product and in subsequent reactions 1,4-dimethoxy-2, 5-dichlorobenzene, 1,4-dimethoxy-2-tert-butyl-dichlorobenzene and 1,4-dimethoxy-2-chlorobenzene. In contrast, anodic chlorinationof 1,4-dimethoxy-2-tert-butylbenzene in CH3CN yields 1,4-dimethoxy-2-tert-butyl-6-chlorobenzene and 1,4-dimethoxy-2-tert-butyI-5-chlorobenzene in about equal amounts. Further chlorination is forestalled and replacement of the tert-butyl group is not observed. 1,4-Dimethoxy-2-tert-butyl-6-chlorobenzene is therefore the main product of the electrochemical route. (C) 2001 Elsevier Science B.V. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 22/09/20 alle ore 10:13:44