Functionalization of anthracene: A selective route to brominated 1,4-anthraquinones

• Kiymet Berkil Akar,
• Osman Cakmak,
• Orhan Büyükgüngör and
• Ertan Sahin

Beilstein J. Org. Chem. 2011, 7, 1036–1045, doi:10.3762/bjoc.7.118

• derivatives that are difficult to prepare by other routes. The studies also reveal the broad range of reactivity and selectivity of the stereoisomeric anthracene derivatives. Keywords: anthracene derivatives; anthracene-1,4-dione; aromatization; bromination; bromoanthracene; methoxyanthracene; silver-induced

• hexabromides 2 and 3 (Scheme 1) [1]. These studies revealed that hexabromides 2 and 3 are good precursors for the preparation of anthracene oxides and methoxyanthracene derivatives by silver ion-induced substitution. Our previous studies revealed that aromatization of hexabromides 2 and 3 showed complete

Highly brominated anthracenes as precursors for the convenient synthesis of 2,9,10-trisubstituted anthracene derivatives

• Osman Cakmak,
• Leyla Aydogan,
• Kiymet Berkil,
• Ilhami Gulcin and
• Orhan Buyukgungor

Beilstein J. Org. Chem. 2008, 4, No. 50, doi:10.3762/bjoc.4.50

• tribromide 12 was transformed to trimethoxy compound 13 and trinitrile 14 by copper-assisted nucleophilic substitution reactions. Keywords: anthracene derivative; bromination; bromoanthracene; cyanoanthracene; methoxyanthracene; Introduction Anthracene derivatives have been extensively investigated in many

• hydroxyanthracenes, and also in the synthesis of anthraquinones. In addition, there are many naturally occurring methoxyanthracene derivatives [31][32]. Copper-assisted nucleophilic substitution of tribromide 12 by cyanide ions easily afforded a cyano derivative of anthracene (14) as the sole product (Scheme 4). The