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Syntheses and spectroscopic characterization of double-armed benzo-15-crown-5 derivatives and their sodium and potassium complexes

2013    Hayvali, Zeliha; Koksal, Pinar

A series of new benzo-15-crown-5 derivatives (1-6) containing formyl and imine groups were prepared. New formyl crown ethers (1 and 2) were prepared by reaction of 4',5'-bis(bromomethyl) benzo-15-crown-5 with 2-hydroxy-3-methoxybenzaldehyde (o-vanillin) and 2-hydroxy-5-methoxybenzaldehyde in the presence of NaOH. New Schiff bases (3-6) were synthesized by the condensation of corresponding aldehydes with 1,3-diaminopropane and 1,4-diaminobutane. Sodium and potassium complexes (1a-6a and 1b-6b) of the crown compounds forming crystalline complexes of 1: 1 (Na+:ligand) and 1: 2 (K+:ligand) stoichiometries were also synthesized. The structures of the aldehydes 1 and 2, imines 3-6 and complexes (1a-3a and 1b-3b) were confirmed on the basis of elemental analyses, IR, H-1- and C-13-NMR, and mass spectroscopy.