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That this process worked so well in Sondheimer's numerous cases probably has two main reasons. On the one hand, the rings involved in annulene chemistry are usually larger and, hence, presumably less strained than in our examples. On the other hand, the generated dehydroannulenes are fully conjugated, and in most cases aromatic.
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note
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We thank Prof. Dr. W. A. König (University of Hamburg) for these separation experiments on the following cyclodextrin phases: heptakis(6-O-tert-butyldimethylsilyl-2,3-di-O-methyl)-β-cyclodextrin, octakis(6-0-methyl-2,3-di-O-pentyl)-β-cyclodextrin, and heptakis(2,6-di-O-methyl-3-O-pentyl)-β-cyclodextrin.
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