In the presence of molecular oxygen or hydrogen peroxide, 1-naphthylamine (1-NA) was catalytically converted into bis(4-oxo-benzo-2-cyclohexen-1-yl) amine (BOBCHA) over metalloporphyrin catalysts through an oxidative-coupling way. UV-vis, IR, NMR, MS, mp determinations and elemental analysis were employed for product characterization. A possible catalytic mechanism based on in situ UV-vis and EPR determinations was proposed. A spectrophotometric method was established for quantitative analysis of the product according to its characteristic absorption at lambda(max) = 465 nm. The influences of reaction conditions, such as solvents, temperature, reaction time, medium alkalinity, as well as species and amount of the catalysts were discussed in detail. (c) 2006 Elsevier B.V. All rights reserved.