The reduction of 9,10-anthraquinones. Part III. Tautomerism of 2-hydroxy-9,10-anthrahydroquinone
Abstract
The tautomeric equilibrium between 2-hydroxy-9,10-anthrahydroquinone and 2,9-dihydroxy-10-anthrone has been examined. Variations of the tautomerism equilibrium constant (K′) with change in pH are related to the acid–base equilibria of the two tautomers. The rate of anthrone formation is dependent upon the nature of the buffer components in the solution, but K′ is independent of this. The structures proposed for two trihydroxy-10-anthrones have been confirmed by n.m.r. spectroscopy.