Anodic Oxidation of Xylenes. Electrochemical Obtention of Cyclohexa-1,4-diene Derivatives

Article abstract of DOI:10.1021/jo00279a026

cis- and trans-3,6-dimethoxy-3,6-dimethylcyclohexa-1,4-dienes obtained by methoxylation of p-xylene were completely separated.The unequivocal structure of the trans isomer was assigned by X-ray diffraction, and the cis:trans ratio is satisfactorily explained by an EEC_rC_p mechanism.When the substrates were p- and o-xylene, the nuclear-addition products were obtained in a two-electron process, but when the substrate was m-xylene, the major muclear-addition product was obtained in a four-electron process.