ISSN:
1573-9171
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Summary 1. 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. 2. 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). 3. 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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00863123
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