The title π-extended TTF derivatives 1 and 2 were prepared from the corresponding diketones by Wittig–Horner reactions. Donor 1 with a naphthalene-1,8-diyl skeleton adopts a butterfly-shaped geometry; its oxidation caused transannular C–C bonding to give the dicationic cyclopropane derivative 42+2+2+, from which 1 was regenerated upon 2e-reduction. The 2,3-diyl isomer 2 possesses, on the other hand, an almost planar π-system and underwent 2-stage 1e-oxidation, thus allowing the isolation of both 2˙+++ and 22+2+2+ as stable salts.
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