Anodic methoxylation of alkylbenzenes

A Century of Organic Electrochemistry

“…113 Anodic substitution and coupling.-Anodic reactions without added mediator may involve a loss of electrons from the substrate or from the solvent The previously mentioned pyridination of anthracene 36 and the methoxylation of furan 45 are examples of the first type; in some oxidations the solvent is oxidized with loss of an electron and a proton and the radical thus formed abstracts a hydrogen atom from the substrate. 114,115 Methoxylation of alkylbenzenes may take place in the side chain or in the nucleus; 4-methylanisole can thus form methoxybenzyl methyl ether or 1,1,4-trimethoxy-4-methylcyclohexa-2,5-diene depending on the medium; when the electrolysis is conducted under conditions where formation of methoxy radicals also takes place, nuclear methoxylation dominates. 116 The methoxylation of methylbenzenes is of industrial importance; BASF oxidizes substituted toluenes in methanolic solution at a carbon anode in a capillary-gap cell to the substituted benzaldehyde dimethylacetal.…”

Study of the Electrochemiluminescence Based on Tris(2,2′-bipyridine) Ruthenium(II) and Alcohols in a Flow Injection System

“…In addition, weaker luminescence could also be obtained if 0.1 M monohydric alcohols were added to the basal solution. Table 1 shows the potentials at which the ECL peaks appeared and the relative maximum luminescence wavelength and I ECL ; there are no significant relationships between the potentials of ECL peaks (12)(13)(14). Recently, Hitmi et al analyzed the product of the oxidation of ethanol (15).…”

“…ECL intensity is known to be highly dependent on the concentration of electrolyte in the carrier solution due to the effect on electrolytic efficiency (20). Sasaki et al reported the effect of changing the supporting electrolyte on the current efficiency of methanol oxidation (13) 3 elicited a large response, it also yielded higher noise. The luminescence intensity decreased when the flow rate was higher than 0.45 ml/min.…”

Electrogenerated Chemiluminescence Based on Tris(2,2′-bipyridyl) Ruthenium(II) with Hydroxyl Carboxylic Acid

“…The study of the oxidation of aliphatic alcohols on a platinum electrode in nonaqueous solution showed that the oxidized product involved alkoxide radicals at a lower electrolytic potential first and then aldehyde ions; the last stage included carboxylic ions at a more positive electrolytic potential (11)(12)(13).…”

“…Weinberg et al reported that the radical processes of carboxylic acid (Eqs. (4) and (5) 12). The brighter luminescences for these organic acids were obtained in 0.2 M K 2 CO 3 or KF solution.…”