Rearrangements of the gibbane skeleton during dehydrogenations with 2,3-dichloro-5,6-dicyanobenzoquinone
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 8,p. 442-443
- https://doi.org/10.1039/c39720000442
Abstract
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.Keywords
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