Derivatives of 3-substituted juglones with either electron-withdrawing or-donating substituents are regioselectively oxidized to o-or p-naphthoquinones using salcomine/air or [bis (trifluoroacetoxy) iodo] benzene, respectively. The structure of the oxidation products was confirmed by chemical transformations. A correlation between chemical shift of the single quinoid proton and the quinone structure was established.