Synthesis of 1,2,5,6- and 1,4,5,8-anthracenetetrone: Building blocks for π-conjugated small molecules and polymers

Figures & data

Scheme 1. Facile synthesis of 1,4,9,10-antracenetrone starting from 1,4-dihydroxy-9,10-anthraquinone (top), molecular structure of 1,2,5,6- and 1,4,5,8-anthracenetetrone (bottom).

Scheme 2. (i) Reduction of 2,6-dihydroxy-9,10-anthraquinone (1a) to 2,6-dihydroxyanthracene (2a). Conditions: NaBH₄, 1 M Na₂CO₃ solution, under argon, RT, overnight. (ii) Oxidation to 1,2,5,6-anthracenetetrone (3a). Conditions: benzeneseleninic acid anhydride, dry THF, under argon, 50 °C, 3 h. (iii) Conversion of 1,8-dihydroxy-9,10-anthraquinone (1b) into 1,4,5,8-tetramethoxyanthracene (2b). Conditions: see Ref. [28], and (iv) Oxidation to 1,4,5,8-anthracenetetrone 3b. Conditions: silica-supported ceric ammonium nitrate (CAN), CH₂Cl₂, RT, 1 h.

Figure 1. Crystal structure of 3b·1,4-dioxane viewed down (a) [100] and (b) [010]. (c) The molecular structure of 3b. C (grey) and O (red) atoms are represented by ellipsoids drawn at the 50% probability levels; H atoms by white spheres of arbitrary radius.

Navale, T. S.; Rathore, R. Synthesis 2012, 44, 805–809. DOI:10.1055/s-0031-1289695.

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