Electrosynthesis and structural characterization of a novel aryl ether trimer

The structure of a novel trimer formed by three p-tert-butyl anisole moieties via the controlled potential electrolysis of p-tert-butyl anisole was determined by X-ray diffraction method. By cyclic voltammetry, we report a multistep electron transfer, each followed by a chemical reaction, resulting in an ECECEC mechanism. Preparative scale oxidation of p-tert-butyl anisole in dry acetonitrile leads to its two first oligomers. The symmetrical dimer, 2,2′-dimethoxy-5,5′-di-tert-butylbiphenyl, shows that the favored coupling sites are those in the ortho position of the methoxy group. The title compound, namely the 1-methoxy-bis-2,3-(2′-methoxy-5′-tert-butylphenyl)-4-tert-butylbenzene crystallizes in triclinic space group P-1 with a = 10.571(3) Å, b = 11.739(1) Å, c = 12.733(2) Å, α = 74.64(1)°, β = 88.71(2)°, γ = 76.58(2)°, V = 1480.8(5) Å3, and Z = 2. The structural analysis reveals that two p-tert-butyl anisole moieties are linked in ortho position on a third p-tert-butyl anisole fragment.