Synthesis of 3-Arylmethyl-p-tropoquinones from 5-Alkoxy-2-(arylmethoxy)-tropones via Homolytic Rearrangement and Oxidation

Article abstract of DOI:10.1246/bcsj.59.1125

The 3-(arylmethyl)-p-tropoquinones were synthesized by starting from the homolytic thermal rearrangement of 2-(arylmethoxy)-5-methoxytropones or 2,5-bis(arylmethoxy)tropones, followed by hydrolysis and oxidation.The half-wave potentials of these tropoquinones were determined by cyclic voltammetry.A remote substituent effect was observed for 3-(4-hydroxybenzyl)-p-tropoquinone, which may be attributable to intermolecular hydrogen bonding.