title: A chiral 28-membered macrocycle with symmetry and structure similar to that of trans-cyclooctene.
abstract: [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.
authors.affiliation: Department of Chemistry and Biochemistry, University of South Carolina, Columbia, South Carolina 29208, USA.
authors.forename: Charles F
authors.initials: CF
authors.lastname: Degenhardt
authors.forename: Mark D
authors.initials: MD
authors.lastname: Smith
authors.forename: Ken D
authors.initials: KD
authors.lastname: Shimizu