SYNTHESIS OF PHENYL SUBSTITUTED CYCLOHEXA-1,4-DIENES AND CYCLOHEXA-2,5-DIENONES BY ANODIC METHOXYLATION OF ALKYLBIPHENYLS

Article abstract of DOI:10.1016/S0040-4020(01)90078-X

The anodic methoxylation of a series of alkylbiphenyls (2-, 3-, 4-methylbiphenyl, 3,3'-, 4,4'-dimethylbiphenyl, 4-ethylbiphenyl and 4,4'-di-tert-butylbiphenyl) carried out under constant current intensity afforded, in a process of two electrons, a number of cis/trans cyclohexa-1,4-dienes and, in a process of four electrons, a number of cyclohexa-2,5-dienones after acidic hydrolysis of the corresponding cyclohexa-1,4-diene ketals.In some cases, side-chain substitution products were also obtained.Probable mechanisms are proposed.