| Abstract |
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The design, synthesis and structural analysis of architecturally new cyclophanes (monomers, dimers,
and trimers) are reported. Variable temperature NMR experiments reveal a regular, tandem
dynamic in the cyclophane 2a that enables its description as a “molecular rocking chair”. The NMR
and X-ray structure investigations show important intra- and intermolecular aromatic  -stacking
interactions. |
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Figure 1. [7.7] cyclophanes, R=H, equatorial-equatorial connection |
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Figure 2. ORTEP diagram and a view of the lattice for metha cyclophanes |
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| Figure 3. ORTEP diagram and a view of the lattice for metha cyclophanes |
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Figure 4. ORTEP diagram and a view of the lattice for para cyclophanes |
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Figure 5. ORTEP diagram and a view of the lattice for para cyclophanes
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Figure 6. ORTEP diagram and a view of the lattice for orto cyclophanes
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Figure 7. ORTEP diagram and a view of the lattice for orto cyclophanes
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| Reference |
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1. Balog, M.; Grosu , I.; Plé , G.; Ramondenc Condamine, E.; Varga, R.
“Design and Synthesis of New Macrocyclic Cyclophanes Using 1,3-Dioxane Units as Bridges: A Molecular “Rocking Chair” |
| J. Org. Chem. 2004, 69, 1337. |
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Design, Synthesis and Structural Analysis of New Cyclophanes Obtained Starting From 1,3-Dioxane Derivatives of 1,4-Diacetylbenzene |
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Abstract
The good yields synthesis and the structural analysis of some new [4.4]cyclophanes obtained from appropriate 1,3-dioxane derivatives of 1,4-diacetylbenzene are reported. The X-ray structures and the NMR investigations revealed important intra and intermolecular pi-stacking and the free or hindered rotation of the aromatic groups. The bordering 1,3-dioxane rings showed an highly unusual resistance for the hydrolysis reaction. |
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| Figure 8. ORTEP diagram of a tetramer cyclophane |
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| Figure 9. ORTEP diagram of a monomer cyclophane |
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| Figure 10. ORTEP diagram of a trimer cyclophane |
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