Abstract
4-Phenylpentacyclo[5. 3. 0. 0 2,5. 0 3,9. 0 4,8]decan-6-one in acetic acid undergoes H 2SO 4-catalyzed rearrangement to give two isomeric acetoxyketones having a novel tricyclo[5. 2. 1. 0 4,8]dec-2-ene ring system besides a small amount of 2,3-dihydro-7-phenyl-1(8 H)-azulenone. The formation of the acetoxyketones can best be accounted by assuming equilibration of several structurally different non-classical bicyclobutonium ion intermediates.
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