Syntheses and Crystal Structures of Novel Diaza-18-Crown-6 Ligands Containing Aromatic Thiol-Derived Side Arms

摘要

The Mannich aminomethylation reaction of aromatic thiols has been used to produce diaza-18-crown-6 ligands containing thiol-derived side arms. Thiophenols were attached to the azacrown through N-CH2-S linkages even in the presence of hydroxy or acetamido groups. Heteroaromatic thiols containing N=C-SH (or NH-C=S) structural fragments were attached to diaza-18-crown-6 by N-CH2-N linkages with the thiol becoming a thione function. X-ray crystal structures provide proof of the N-CH2-S and N-CH2-N linkages for the products of reactions with thiophenols and heteroaromatic thiols, respectively.