Action of alkaline sodium hypochlorite on a 1,2,3,4-tetrahydro-9(10H)-acridinone: X-ray structure of a novel, vicinal cis-diol product

The oxidation of tetrahydro-9(10H)-acridinone by sodium hypochlorite afforded a highly fluorescent, yellow crystalline product that was characterized by 1H n.m.r., mass spectrometry, and single-crystal X-ray diffraction, as a vicinal cis-diol. A remarkable feature of the structure is the variety of hydrogen-bonding types observed. These include normal intra- and intermolecular hydrogen bonds, together with hydrogen bonds bifurcated into intra- and intermolecular interactions at the same centre