Gibbanes in which ring A is aromatic react with 2,3-dichloro-5,6-dicyanobenzoquinone giving allylic carbonium ions (viaΔ4b-enes) which then undergo Wagner–Meerwein rearrangement; in 7-hydroxy-compounds, the 7,8-bond migrates to C-6 to give a 7-ketone, whereas in 7-deoxy-gibbanes, the 9,9a-bond migrates to position 4b to give a 9a,10-ene.
B. E. Cross and R. E. Markwell, J. Chem. Soc., Chem. Commun., 1972, 442 DOI: 10.1039/C39720000442
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