2008 Volume 76 Issue 12 Pages 874-879
Anodic oxidation of a furan derivative was accomplished in cycloalkane-based thermomorphic (CBT) electrolyte solutions. In the CBT system, hydrophobic phase-tagged substrates were efficiently electrolyzed in the reversibly immixed mono-phasic state followed by on-cooling phase-separation of the tagged product as the cycloalkane solution separated from the polar electrolyte solutions. In the case of anodic oxidation of the phase-tagged furanyl compound, a 3,5-didocosyloxybenzyl tag that possessed higher oxidation potential and high hydrophobicity worked efficiently for achieving the selective anodic oxidation of the furanyl moiety. The electrolytic products were also successfully subjected to catalytic hydrogenation, which is generally difficult for solid-supported substrates. The product was separated from the CBT electrolyte solution simply by on-cooling phase separation.