The new pentadentate ligand 1,3-bis[N-2-(2′-pyridylethyl)formimidoyl]-2,5-dihydroxybenzene (1) was prepared in five steps from 2,6-dimethylphenol in 21% overall yield. Reaction of 1 with CuII(Clo4)2·6H2O gave the unexpectedly stable hydroquinone-containing binuclear Cu(II) complex [2,6-bis[N-2-(2′-pyridylethyl)formimidoyl]-4-hydroxy-1-phenolato]biscopper(II) bisperchlorate (8). The crystal and molecular structure of 8 was determined by X-ray analysis. The complex crystallizes in the triclinic space group [formula omited], with Z = 2 in a unit cell of the following dimensions: a = 9.399 (2) Å, b = 10.469 (1) Å, c = 14.612 (4) Å, α = 102.72 (2)°, β= 100.71 (2)°, γ = 104.60(2)°. Surprisingly high reactivity of 8 was observed in catalytic oxidations of hydroquinones and α-hydroxy ketones using molecular oxygen as the oxidant. A mechanistic discussion is provided. © 1990, American Chemical Society. All rights reserved.