FLUORIDE SALTS-ALCOHOLS-ALUMINA AS REAGENTS FOR NUCLEOPHILIC-SUBSTITUTION OF CHLORINE ATOMS FOR ALKOXY GROUPS IN 2,3-DICHLOROSUBSTITUTED JUGLONES, NAPHTHAZARINES, AND QUINIZARINES

Direct displacement of chlorine atoms by alkoxy groups in 2,3-dichlorosubstituted juglones (5-hydroxy-1,4-naphthoquinones), naphthazarines (5,8-dihydroxy-1,4-naphthoquinones), and quinizarines (1,4-dihydroxy-9,10-anthraquinones) is generally ineffective, however high yields are obtained when methanol or cellosolves activated by fluoride anion are used as nucleophiles and the reaction goes in the presence of alumina.