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A compound containing a carbon–nitrogen double bond. Reversible condensation of an aldehyde with a primary amine gives an imine and water under suitable conditions.

An imine whose imine carbon bears two carbon substituents. Hydrolysis passes through a carbinolamine and gives a ketone.

Each primary amine arm of 2 condenses with one aldehyde 1, eliminating three waters overall and forming a tripodal tris(pyridylimine) ligand $L$. The three imine nitrogens and the three adjacent pyridine nitrogens chelate one Fe(II), giving $[\mathrm{Fe}L{]}^{2+}$, with three outward-facing terminal pyridines still free. The central tertiary amine is the tethering apex, not a seventh donor in the six-coordinate model.

The Fe coordination is approximately octahedral and is propeller-chiral: three bidentate chelates can have $\Delta$ or $\Lambda$ configuration. Achiral starting components and conditions give a racemic population unless a separate resolving influence is introduced. imine condensation and metal coordination cooperate in subcomponent self-assembly; the metal template selects the convergent ligand arrangement.

The oxime is reduced at its C=N bond rather than cleaving N–O: hydride addition to the imine carbon followed by protonation gives an N-substituted hydroxylamine. In a chair-like model of the cis-fused ring system, the fused framework and methyl group make the two faces inequivalent. The favoured hydride trajectory accesses the face that places the newly installed C–H bond behind the original drawing and the retained C–NHOH bond in front, giving D. It avoids the more congested trajectory into the folded bicyclic framework; a flat hexagon comparison alone misses this facial distinction.

The existing methyl and junction centres are retained. The selectivity is therefore diastereoselective substrate control, not enantioselectivity from sodium cyanoborohydride, which is achiral. For a racemic starting bicycle the same relative stereochemical preference gives a racemic pair of D enantiomers.

Reversible imine formation and disulfide exchange provide two suitable dynamic covalent chemistry reactions.

An aldehyde and a primary amine can reversibly form an imine with loss of water:Multifunctional components can build rings or cages. Acid catalysis, solvent and water activity must permit both formation and hydrolysis or exchange, so that initially incorrect connections can rearrange.

For disulfide exchange, a thiolate attacks a disulfide and substitutes one sulfur-containing fragment:Suitable pH, redox conditions and exchange kinetics let a library of connectivities equilibrate. A template that stabilizes one assembly can shift the library towards it. Reversibility under the actual conditions is essential: calling a covalent reaction “dynamic” does not make a kinetically trapped product mixture equilibrate.

The hydride reagent $\mathrm{NaB}{\mathrm{H}}_3\mathrm{CN}$. Its comparatively mild reactivity permits selected imine and iminium reductions.

Reversible formation of covalent ligands and metal coordination bonds from simpler components in the same mixture. imine condensation around a metal template is a common example.