| Abstract
| - An efficient synthesis of the two diastereomeric tetrakisfulleroids 14a and 14b is described startingfrom the readily accessible trans-1 bis-Diels−Alder adduct 12. The challenging issue of generatingmultiple bond scissions regiochemically within the fullerene framework, here as [5,6] open systems(fulleroids), is simplified into performing two separate regiocontrol phases. The initial bisadduct12 can only undergo syn or anti photochemically promoted intramolecular tandem [4 + 4] andretro [2 + 2 + 2] rearrangements, giving the two isomers 14a and 14b in an unexpected 1:4 ratio.Interestingly, the UV−vis absorption spectra of these two isomers are quite different even thoughtheir local chromophore perturbations are distant from each other.
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