Products of photoreduction of 9,10-phenanthrenequinone in the presence of N,N-dimethylanilines and polymethylbenzenes

Photoreduction of 9,10-phenanthrenequinone (PQ) in the presence of p-substituted N,N-dimethylanilines and polymethylbenzenes affords corresponding phenolethers as primary products. In the subsequent process shielded from light, phenolethers, which were formed by photoreaction of PQ with N,N-dimethylanilines, were quantitatively converted to give corresponding ketols. Phenolethers of 9,10-phenanthrenequinone and polymethylbenzenes are rearranged only under irradiation and in the presence of second molecule of PQ to form ketols. Stability of phenolethers is determined by redox properties and structure of hydrogen donors.