Acceleration and Selectivity of 1,3-Dipolar Cycloaddition Reactions Included in a Polar [4 + 2] Octa-imine Bis-calix[4]pyrrole Cage.

ABSTRACT: We describe the quantitative self-assembly (>90%) of a [4 + 2] octa-imine cage (1) in a CDCl₃:CD₃CN 9:1 solvent mixture containing 0.5% of acetic acid. Cage 1 is based on two identical aryl-extended calix[4]pyrrole units linked through eight dynamically reversible imine bonds. Cage 1 forms thermodynamically and kinetically highly stable inclusion complexes featuring 1:1 and 2:1 stoichiometry with suitable para-substituted pyridine-N-oxides. The ability of 1 for the pairwise inclusion of two different pyridine-N-oxides led us to investigate its properties as a reactor vessel. The coinclusion of 4-azido pyridine-N-oxide and 4-ethynyl pyridine-N-oxide did not produce a detectable acceleration of their 1,3-dip

SUBMITTER: Li Y 

PROVIDER: S-EPMC11862939 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature