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[reaction: see text] A bridged N,N-di(aryl)-1,2,4,5-benzenediimide was synthesized in which restricted rotation led to two diasteriomeric conformations at room temperature. The more stable syn-macrocycle is achiral, whereas the strained anti-macrocycle possesses planar chirality similar to that of trans-cyclooctene. The structure was characterized by X-ray crystallography, and the enantiomers were resolved by chiral chromatography.
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Degenhardt et al. (2002) studied this question.
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