T~tmrr'~1, the heat of hydrogenation of the first double bond of barrelene is 9 kcal/mol greater than for the remaining two double bonds, a value that is to be regarded as a measure of the destabilization of this molecule. Beyond doubt, therefore, the "dihydrobarrelene" (6) is lower in energy than (8) by several kcal/mol even though it contains an exocyclic double bond that must increase the strain191. Such an energy difference is more than enough to freeze in completely the arene oxide form (6).

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