A series of layered cyclophanes where an anthracene ring is stacked in different modes with the same or other π-systems has been synthesized by the Hofmann elimination method or photodesulfurization for studying the transannular π-electronic interaction. Photochemical and thermal interconversions have been observed between syn-(1,4)anthracenophane and its isomer and have been discussed with reference to the X-ray crystal data. From the electronic spectra it has been established that the transannular interaction increases with overlapping between the two faced aromatic rings and that when the overlap between the two chromophores is the same, the interaction increases relative to the dimension of the faced chromophore.
An unusual Diels-Alder reaction was observed to give intramolecular cycloadducts during the syntheses of triple-layered cyclophanes containing anthracene nucleus. The structure of the product was determined by spectral and X-ray crystal analyses. The crystal is monoclinic, P21/c, with a=15.896, b=8.937, c=18.575 Å, β=120.31°, Z=4. The crystal structure was determined by the direct method using the MULTAN program and refined by the block-diagonal least-squares method to an R index of 0.081. The structure of the molecule is fairly strained.
Das Produkt einer ungewöhnlichen Diels‐Alder‐Reaktion der Ammoniumhydroxide (I) und (II) in siedendem Xylol und in Gegenwart von Phenothiazin zeigt die Struktur (III).
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