Related Experiment Video
Updated: Aug 19, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Synthesis, structure, and contrasting chiroptical properties of large trianglimine macrocycles
Marcin Kwit1, Paweł Skowronek, Halina Kołbon
1Department of Chemistry, A. Mickiewicz University, Poznań, Poland.
Abstract:
We have synthesized a number of large trianglimine macrocycles (3a-3f) using our methodology of (3+3) cyclocondensation of (R,R)-trans-1,2-diaminocyclohexane (1) with rigid aromatic dialdehydes (2a-2f), having benzene, biphenyl, terphenyl, styrene, or divinylbenzene spacers. The structures of these chiral macrocycles have been analyzed using computational methods as well as CD spectroscopy. Whereas trianglimines 3a-3d gave uniformly negative exciton Cotton effects, as expected, styrene- and divinylbenzene-based trianglimines 3e and 3f gave opposite-sign exciton Cotton effects. Their contrasting CD behavior was traced by computational methods to subtle differences in the relative orientation of the electric dipole transition moments in the chromophores of the trianglimines. The presence of low-intensity long-wavelength electronic transitions having large rotational strengths in the electronic spectra of 3e and 3f can be accounted for by the symmetry properties of the trichromophoric macrocycles.
Related Concept Videos
Stereoisomerism of Cyclic Compounds
Prochirality
Chair Conformation of Cyclohexane
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...
Conformations of Cyclohexane
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal tetrahedral value,...
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group with both...
Molecules with Multiple Chiral Centers

![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)