Supramolecular Construction of an Aldehyde–Cyclobutane via the Solid State: Combining Reversible Imine Formation and Metal–Organic Self-Assembly

A combination
of metal–organic self-assembly and reversible
imine formation is used to achieve an organic synthesis via the solid
state. Imine bond formation is employed to install a pyridyl to the
alkene trans-cinnamaldehyde while Ag­(I) ions are
used in a second step to assemble the pyridyl-functionalized alkene
into a geometry in the solid state for an intermolecular [2 + 2] photodimerization.
The alkene undergoes the cycloaddition reaction via a 1D coordination
polymer to generate a pyridyl-functionalized cyclobutane stereoselectively
and in quantitative yield. Removal of the pyridyl group affords the
aldehyde-functionalized cyclobutane α-truxilaldehyde.