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Juglophen: a tetradentate non-innocent electron sponge naphthoquinone-imine ligand and its reduced and oxidized nickel complexes [Ni(jp)]−,0,+

“…Bukhtoyarova et al described a related coupling of 1,5-dihydroxynapthalene with aniline in the presence of an oxidation reagent cocktail containing K 3 Fe(CN) 6 , HIO 3 or NaIO 4 generating N-phenyl-5hydroxy-1,4-naphthoquinone-4-imine via electrophilic attack of generated N-radical cation intermediates at 1,5dihydroxynapthalene. 42,43 When we applied K 3 Fe(CN) 6 . HIO 3 as oxidant towards a mixture of 1,5-dihydroxynapthalene and o-phenylenediamine, our target juglophen (1) or an isomer of it was observed in the mass spectrum among other by-products, however elemental analysis and X-ray fluorescence spectroscopy (XRF) indicated a high content of elemental iodine and other impurities, which could not be fully separated from 1.…”