A chiral 28-membered macrocycle with symmetry and structure similar to that of trans-cyclooctene.

[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.