THE AQUEOUS PHOTOCHEMISTRY OF 2,6-DIMETHYLPHENOL - EVIDENCE FOR THE FRAGMENTATION OF THE ALPHA-C-C BOND

A study of the photochemical behaviour of 2,6-dimethylphenol in aerate d aqueous solution upon excitation at 270 nm has been undertaken. High -performance liquid chromatography (HPLC) analyses indicated the prima ry formation of 2,6-dimethylbenzoquinone and the para-para coupling di mer as major products; two isomeric products resulting from ct C-C sci ssion were also observed. They account for about 20% of the conversion . Only the dimer was observed when the irradiation was carried out und er deaerated conditions. The photoreaction has been shown to result fr om an electron ejection process leading to phenoxyl radical and solvat ed electron. The results indicate that O-2(.-) and HO2- are among the species involved in the formation of the oxidized products and particu larly those arising from the cleavage of the aromatic ring. (C) 1998 E lsevier Science S.A. All rights reserved.