Abstract
Abstract Adamantane-2,4-bis(p-quinone methide) and -2,6-bis(p-quinone methide) were synthesized by the reaction of adamantane-2,4-dione and -2,6-dione, respectively, with lithium 4-lithio-2,6-di-t-butylphenoxide, followed by dehydration. Their structures were established by spectroscopic and X-ray crystallographic analyses. Having a distance (2.47 Å) between C2 and C4 longer than that (ca. 1.9 Å) between C1 and C3 of cyclobutane-1,3-bis(p-quinone methide)s, adamantane-2,4-bis(p-quinone methide) was found to show a clear through-space interaction (homoconjugation) and to form a σ-bond at its bis(anion radical) stage upon both chemical and electrochemical reduction. On the other hand, adamantane-2,6-bis(p-quinone methide), which has a long distance and near orthogonal arrangement between the quinone methide chromophores, shows a through-bond interaction, though it is weak.
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