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Abstract
Six 3-methylpyridine zwitterions and six quinoline zwitterions were synthesized through the reaction of 4-hydroxycoumarins, p-benzoquinone and the corresponding N-aromatics. The novel pseudo-cyclic face-to-face rigid structure of the zwitterion was elucidated by 1H-NMR at different temperatures, and assumed to be caused by both the intramolecular ion pair attraction and the steric interaction.
Highlights
The compounds with cyclic structures derived from the [2.2] paracyclophane backbone 1(Figure 1) have stimulated considerable interest due to their special properties and applications. 4,12Bis(diphenylphosphino)-[2.2]-paracyclophane was shown to be an excellent transition metal ligand for the catalytic asymmetric hydrogenation of carbonyl groups [1,2,3,4]
In a recent communication [13], we reported the synthesis of zwitterionic 4-hydroxycoumarin derivatives
We describe the novel pseudo-cyclic face-to-face rigid structures of these zwitterions (Figure 2)
Summary
The compounds with cyclic structures derived from the [2.2] paracyclophane backbone 1. (Figure 1) have stimulated considerable interest due to their special properties and applications. The bridge-fluorinated paracyclophanes display intriguing chemical reactivity [5,6,7] and commercial applications [8,9]. The bridging ligands derived from paracyclophane have afforded the opportunity to investigate the role of. It is believed that the cyclic face-to-face rigid structure of the paracyclophane moiety plays an important role in properties of these derivatives. In a recent communication [13], we reported the synthesis of zwitterionic 4-hydroxycoumarin derivatives. We describe the novel pseudo-cyclic face-to-face rigid structures of these zwitterions (Figure 2)
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