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
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
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Graphical Abstract
Scheme 1:
Photobromination of 9,10-dibromoanthracene.