Highly selective catalytic preparation of bis(4-oxo-benzo-2-cyclohexen-1-yl) amine from 1-naphthylamine oxidation over metalloporphyrin catalysts by molecular oxygen under air pressure and by hydrogen peroxide

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 λmax = 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.

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