1,4-Naphthoquinone undergoes diene condensation with pentacene both in the 6, 13-positions (middle ring of pentacene) and in the 5,14-positions (second ring of pentacene). This results in the formation of two adducts: 5a,6,13,13a-tetrahydro-6,13[2′,3′]-naphthalenopentacene-5,14-dione (III) and 5a,6,15,15a-tetrahydro-6,15-o-benzenohexacene-5-16-dione (IV). The structures of the isomers isolated were confirmed by spectroscopic data.
The following were synthesized for the first time: the adducts (III) and (IV), 6,13-dihydro-6,13[2′,3′]-napthalenopentacene-5,14-dione (II),6,13-dihydro-6,13[2′,3′]-naphthalenopentacene-5,14-diol (V), and the corresponding quinhydrone (VIII); the hydroquinone (V) was characterized also as its diacetyl derivative (VI).
Increase in the number of linearly annelated rings in the hydrocarbon part of the bridged hydroquinone 5,12-dihydro-5,12-o-benzenonaphthacene-6,11-diol (VII) so as give the hydroquinone (V) leads to a more stable molecule.
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Antik, L.V., Klabunovskii, E.I., Balandin, A.A. et al. Synthesis and reactions of 6,13-dihydro-6,13[2′, 3′]-naphthalenopentacene-5,14-dione. Russ Chem Bull 13, 1167–1173 (1964). https://doi.org/10.1007/BF00863123