L. Appelbaum, D. Danovich, G. Lazanes
Feb 23, 2001
Citations
0
Influential Citations
14
Citations
Journal
Journal of Electroanalytical Chemistry
Abstract
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 CCl 4 but not in CH 3 CN. 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 CH 3 CN 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.