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.

Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (96 K)Download as PowerPoint slide