β-Ionylideneacetaldehyde (I) can easily be isomerized thermally to a tricyclic ketone (IV), probably via an initial E-to-Z isomerization of the double bond adjacent to the carbonyl group, followed by a [1,5]sigmatropic hydrogen shift; the resulting keten (III) interacts with the double bond of the cyclohexene ring to give the [2 + 2] cycloadduct (IV).
A. Smit, J. G. J. Kok and H. W. Geluk, J. Chem. Soc., Chem. Commun., 1975, 513 DOI: 10.1039/C39750000513
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