The γδ-unsaturated ketone (4) rearranges thermally in two ways:above 200° a retro-Claisen reaction leads to practically quantitative conversion into the allylvinyl ether (9), while between 150 and 180°, a Cope reaction of the enol (10) allows quantitative isolation of the bicyclo[3,3,1]nonenone (11); the none-enolisable aldehyde (3) gives only the ether (5) between 150 and 300°.
Y. Bessiere-Chretien and C. Grison, J. Chem. Soc., Chem. Commun., 1973, 549 DOI: 10.1039/C39730000549
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