Synthesis and reactions of trinitro-9,10-phenanthrenequinone derivatives

The reaction of 2,4,7-trinitro-9,10-phenanthrenequinone with CuCl in aqueous dimethylformamide or dimethyl sulfoxide at room temperature, followed by acidification, gave a stable red complex of 2,4,7-trinitro-9,10-dihydroxyphenanthrene with a solvent molecule. On heating in a polar aprotic solvent in the presence of CuCl or other metal salt, 2,4,7-trinitro-9,10-phenanthrenequinone underwent benzilic acid rearrangement with formation of 2,4,7-trinitrofluorenone. The nitration of 9,10-sulfuryldioxyphenanthrene and subsequent decomposition of cyclic sulfates afforded previously unknown 1,3,6-trinitro- and 1,8-dinitro-9,10-phenanthrenequinones.