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Article

Synthesis of New Anthracene Derivatives

Osman Cakmak,*^† Ramazan Erenler,^† Ahmet Tutar,^‡ and Nuray Celik^†

Department of Chemistry, Faculty of Art and Science, Gaziosmanpasa University, 60240 Tokat, Turkey, and Department of Chemistry, Faculty of Art and Science, Sakarya University, Turkey

J. Org. Chem., 2006, 71 (5), pp 1795–1801

DOI: 10.1021/jo051846u

Publication Date (Web): February 4, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

†

Gaziosmanpasa University.

‡

Sakarya University.

, ocakmak@gop.edu.tr

Abstract

An efficient synthesis is described for hexabromoanthracenes 3 and 4 by direct bromination of 9,10-dibromoanthrecene 2. Whereas base-induced elimination of hexabromide 3 with t-BuOK gave 2,3,9,10-tetrabromoanthracene 5, the reaction of hexabromide 4 with DBU afforded 1,3,9,10-tetrabromoanthracene 6 as the sole product. Tetrabromide 5 was also obtained by aromatization of 1,4-dinitroxy-2,3,9,10-tetrabromo-1,2,3,4-tetrahydroanthracene 17. Efficient and convenient synthetic routes are described for the preparation of dinotroxy 17, dimethoxy 23, and dihydroxides 18 and 19 with silver-induced substitution of hexabromides 3 and 4. The hydroxy compounds 19 and 18 were converted to diepoxide 20 and monoepoxide 21, respectively, with sodium methoxide. Base-promoted aromatization of dimethoxide 23 afforded dibromomonomethoxides 26 and 27. Bromoanthracenes and isomeric arene oxides constitute valuable precursors for the preparation of functionalized substituted anthracene derivatives that are difficult to prepare by other routes.