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-dichloro substituted 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 o btained when methanol or cellosolves activated by fluoride anion are u sed as nucleophiles and the reaction goes in the presence of alumina.