Two new highly substituted hydroquinones (1,4-bis(dimethylphosphonato)-2,5-dichloro-3,6-dihydroxybenzene (2a) and 1,4-bis(diethylphosphonato)-2,5-dichloro-3,6-dihydroxybenzene (2b)) were synthesized. Treatment of 2a-b with K2S2O8 under basic conditions led to oxidation of the hydroquinone and substitution of the chlorines by hydroxy groups. Treatment of reaction mixtures with excess HCl led to isolation of 2,5-dihydroxy-1,4-quinones appended with two phosphonate groups (H23a and H23b). Treating 2a-b with ammonia in the presence of CuCl2 and air led to a catalytic oxidation/substitution process which produced bis(phosphonato)-2,5-diamino-1,4-quinones 4a-b. Compounds H23a and H23b readily form salts when reacted with ammonia or alkali metal hydroxides. Ammonium salts (NH4)23a and (NH4)23b are presented here. All compounds were characterized by FT-NMR (1H, 13C and 31P) spectroscopy and mass spectrometry. In addition, compounds 2a, H23a, H23b, (NH4)23a and (NH4)23b and 4a were characterized by single crystal X-ray diffraction methods. Relevant cyclic voltammetry is presented.

Synthesis and physicochemical properties of 2,5-dihydroxy- and 2,5-diamino-1,4-quinones appended with two phosphonate groups

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