Dehydration of tertiary bicyclo[3.3.1]nonan-9-ol-2-ones. Rearrangement to cis-fused hexahydroinden-1-ones

Add time:09/01/2019    Source:sciencedirect.com

Dehydrations of the anti-ketol 5 and its isomer 10 have been studied. In both cases the 1-hydrindenones 6 and 7 have been almost quantitatively obtained (1:1 ratio) through skeletal rearrangement of the kinetically favoured 9-methylene bicyclononane 9. This strongly supports the hypothesis of a stepwise rearrangement driven by the relative stabilities of the involved carbonium ions.

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