Abstract
The first synthesis of tetracene starts with a condensation of succinic acid with phthalic anhydride in the presence of sodium acetate. The resulting ethinediphthalide (I) re-arranges in the presence of sodium ethoxide to the disodium salt of dihydroxytetracenequinone (isoethinediphthalide, II) and to bisdiketohydrindene (III);1 oxidation of the latter is said also to lead to dihydroxytetracenequinone.2 Zinc-dust distillation of (II) yields tetracene (IV) in addition to 5,12-dihydrotetracene (V) which is formed exclusively if the reduction is carried out with hydriodic acid.2
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Reference
Clar, E., J. chem. Soc. 2440 (1949).
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© 1964 Springer-Verlag Berlin Heidelberg
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Clar, E. (1964). Hydrocarbons with Four Linearly Annellated Benzene Rings. In: Polycyclic Hydrocarbons. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-01665-7_23
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DOI: https://doi.org/10.1007/978-3-662-01665-7_23
Publisher Name: Springer, Berlin, Heidelberg
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