Ein neues, Deltaphan und bandförmige Cyclophane

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Abstract
A New Deltaphane and Ribbon‐Shaped CyclophanesThe reaction of the fourfold functionalized [3.3][3.3]metacyclophane 8 with tosylamide monosodium salt leads to a new deltaphane in quantitative yield. An X‐ray analysis confirms the belt‐shaped structure of 3. Moreover, a series 10–15 of well‐soluble belt‐shaped macrocycles with up to 21 interconnected benzene rings were detected. The intermediate [3.3][3.3]metacyclophane 4 shows remarkably short distances to enclosed toluene, one toluene molecule acting twice as a π acceptor and once as a π donor. Competition experiments with benzene demonstrate the dependence of conformational behaviour on the solvent.