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Furanophane 2 has been converted via benzyne addition/aromatisation into the naphthafurophanes 5 and 8. The X-ray structure of the diepoxydinaphthofurophane intermediate 6 is also reported. A preliminary dynamic NMR analysis of the conformational behaviour of 8 is presented.
The cycloaddition of two moles of benzyne with any two non diametrically opposite furan units of 1 in ananti geometry yields a chiral macrocycle. The chiral anti-1,3-bis-adduct 2 has been isolated, characterised by X-ray crystallography, and converted into the corresponding dinaphthafurophane 4. The X-ray analysis of 4 shows the crystals to contain only a single enantiomer i.e. 4 undergoes spontaneous...
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