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| - Metathesis Reaction of Formaldehyde Acetals: An Easy Entryinto the Dynamic Covalent Chemistry of CyclophaneFormation
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| - The acid-catalyzed transacetalation of formaldehyde acetals (formal metathesis) is a suitablereaction for the generation of well-behaved Dynamic Libraries of cyclophane formals. The composition ofthe equilibrated mixtures solely depends on concentration, and is totally independent of whether thefeedstock is any of the pure cyclic oligomers, or a mixture of oligomers/polymers. Effective Molarities relatedto the formation of the lower cyclic oligomers were directly measured as their equilibrium molar concentrationsabove the critical monomer concentration. The finding that silver cation acts as a selective binder towardthe cyclic dimer C2, coupled with the “proof reading and editing” capability of our quickly equilibrating system,translated into significant amplifications of C2 when the equilibrated mixtures were exposed to the actionof the silver template. These results highlight the potential of Dynamic Combinatorial Chemistry as a powerfultool for the preparation in synthetically useful amounts of an otherwise elusive macrocyclic compound.The possibility of using a mixture of high molecular weight byproducts as feedstock adds considerably tothe practical value of the procedure.
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