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• W2018972007 abstract "Durch [4 + 2]-Cycloaddition von Maleinsäureanhydrid, 2-Chlorpropenoylchlorid bzw. (E)-Dichlorethen an 1,4-Di- (3a) und 1,4,5,8-Tetramethoxyanthracen (3b) entstehen die Dihydroethanoanthracene 4, 5 bzw. 8. Dem überwiegenden der Maleinsäureanhydrid-Addukte 4a wird aufgrund des ESR-Spektrums der Radikalkationen 4a+˙ die exo-Konfiguration zugeordnet. Die Cycloaddukte 5 und 8 werden über die Ketone 6 bzw. Dihydroethenoanthracene 9 in die Dihydroethanoanthracene 10 übergeführt. Aluminiumchlorid in Nitromethan oxidiert die α-Methoxydihydroethanoanthracene 4, 6a, 8 und 10 zu Radikalkationen, deren ESR-Spektren analysiert werden. Neben den erwarteten Protonen-Hyperfeinaufspaltungen des 1,4-Dimethoxybenzolrings beobachtet man weitreichenden Transfer von Spindichte zum unsubstituierten Benzolring [a(4H) = 0.008–0.010 mT] sowie zu den syn-[10a+˙: a(2H) = 0.013 mT] und anti-Protonen [a(2H) = 0.059–0.069 mT] der Ethanobrücke. Von den Radikalkationen mit zwei 1,4-Dimethoxybenzolringen zeigen die aus 4b und 10b erhaltenen keine dynamischen ESR-spektroskopischen Phänomene. Dagegen wird in 8b+˙ das ungepaarte Elektron rasch bezüglich der Hyperfeinaufspaltungs-Zeitskala zwischen den 1,4-Dimethoxybenzolringen ausgetauscht. Die Abhängigkeit der Austauschfrequenz von der Temperatur und der Aluminiumchlorid-Konzentration weist auf Ionenpaar-Effekte hin. Intramolecular Interactions in Radical Cations of Di- and Tetra(α-methoxy)-9,10-dihydro-9,10-ethanoanthracenes [4 + 2]-Cycloaddition of maleic anhydride, 2-chloropropenoyl chloride and (E)-dichloroethene to 1,4-di- (3a) and 1,4,5,8-tetramethoxyanthracene (3b) yields the dihydroethanoanthracenes 4, 5, and 8, respectively. The predominant maleic anhydride adduct 4a is assigned the exo-configuration on the basis of the ESR spectrum of the radical cations 4a+˙. The cycloadducts 5 and 8 are converted to the dihydroethanoanthracenes 10 via the ketones 6 or the dihydroethenoanthracenes 9, respectively. Aluminium chloride in nitromethane oxidizes the α-methoxydihydroethanoanthracenes 4, 6a, 8, and 10 to radical cations the ESR spectra of which are analyzed. Besides the expected proton hyperfine splittings of the 1,4-dimethoxybenzene moiety, one observes long-range transfer of spin density to the unsubstituted benzene ring [a(4H) = 0.008–0.010 mT] as well as to the syn-[10a+˙: a(2H) = 0.013 mT] and anti-protons [a(2H) = 0.059–0.069 mT] of the ethano bridge. Of the radical cations possessing two 1,4-dimethoxybenzene rings, 4b and 10b do not exhibit dynamic ESR spectroscopic phenomena. On the other hand, the unpaired electron is exchanged rapidly (with respect to the hyperfine splitting time scala) between the 1,4-dimethoxybenzene rings of the radical cation 8b+˙. The dependence of the exchange frequency on the temperature and the aluminium chloride concentration is indicative of ion-pair effects." @default.
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• W2018972007 date "1986-08-01" @default.
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• W2018972007 title "Intramolekulare Wechselwirkungen in Radikalkationen von Di- und Tetra(α-methoxy)-9,10-dihydro-9,10-ethanoanthracenen" @default.
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• W2018972007 doi "https://doi.org/10.1002/cber.19861190803" @default.
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