TY - JOUR
T1 - An electrochemical aromatic chlorination, comparison with electrophilic reaction
AU - Appelbaum, L.
AU - Danovich, D.
AU - Lazanes, G.
AU - Michman, M.
AU - Oron, M.
PY - 2001/2/23
Y1 - 2001/2/23
N2 - 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 chlorination of 1,4-dimethoxy-2-tert-butylbenzene in CH3CN yields 1,4-dimethoxy-2-tert-butyl-6-chlorobenzene and 1,4-dimethoxy-2-tert-butyl-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.
AB - 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 chlorination of 1,4-dimethoxy-2-tert-butylbenzene in CH3CN yields 1,4-dimethoxy-2-tert-butyl-6-chlorobenzene and 1,4-dimethoxy-2-tert-butyl-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.
KW - Anodic chlorination
KW - Aromatic ethers
KW - Electro-chlorination
UR - http://www.scopus.com/inward/record.url?scp=0035936661&partnerID=8YFLogxK
U2 - 10.1016/S0022-0728(00)00465-4
DO - 10.1016/S0022-0728(00)00465-4
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AN - SCOPUS:0035936661
SN - 0022-0728
VL - 499
SP - 39
EP - 47
JO - Journal of Electroanalytical Chemistry
JF - Journal of Electroanalytical Chemistry
IS - 1
ER -