Fluoride salts-alcohols-alumina as reagents for nucleophilic substitution of chlorine atoms for alkoxy groups in 2, 3-dichlorosubstituted juglones, naphthazarines, and …

VP Anufriev, VL Novikov

Index: Anufriev, Victor Ph.; Novikov, Vyacheslav L. Tetrahedron Letters, 1995 , vol. 36, # 14 p. 2515 - 2518

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Citation Number: 34

Abstract

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.