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The doubly-decked [8]annulene 11 has been prepared in 13 steps from the known diketone 15. The scheme takes advantage of the aramia ting capacity of the Cook-Weiss reaction and the ability of semibullvalenes to undergo thermal isomerization to cyclooctatetraenes. The bis(semibullvalene) 12 is both conformationally dynamic and subject to very rapid Cope rearrangement.The energetics of inversion within its interconnective cyclooctane ring have been elucidated by variable-temperature NMR spectroscopy. The structural nature of 11 has been made clear by a combination of molecular mechanics calculations and