Synthesis of hydroquinone diacetates from polycyclic aromatic quinones

Abstract

A convenient general synthesis of hydroquinone diacetates from polycyclic aromatic quinones through reduction with sodium borohydride in dimethylformamide is described. Improved methods for the synthesis and chromatographic separation of the 1,6-, 3,6-, and 6,12-diones of benzo[a]pyrene are also described. 270 MHz N.m.r. spectroscopy is employed to confirm the structural assignments of the latter and the use of this technique is proposed for the characterization of carcinogen metabolites.