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We suggest four new benzene dimers, (C(6)H(6))(2), all featuring one or more cyclohexadiene rings trans-fused to 4- or 6-membered rings. These hypothetical dimers are 50-99 kcal/mol less stable than two benzenes, but have computed activation energies to fragmentation ???27 kcal/mol. A thorough search of potential escape routes was undertaken, through cyclobutane ring cleavage to 12-annulenes, sigmatropic 1,5-H-shifts, electrocyclic ring-openings of the 6-membered rings, and Diels-Alder dimerizations. Some channels for reaction emerge, but there is a reasonable chance that some of these new benzene dimers can be made.

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Hoffmann1 reports on a number of new benzene dimer structures, notably 5-8, whose RIJCOSX-MP2/cc-pVTZ2 structures are shown in Figure 1. A few of these new dimers are only somewhat higher in energy than the known dimers 1-4. The energies of these dimers, relative...
A. U. Rogachev, X.-D. Wen, R. Hoffmann Journal of the American Chemical Society 2012, 134, 8062. (Paywall)Contributed by Steven Bachrach.Reposted from Computational Organic Chemistry with permissionHoffmann1 reports on a number of new...