Bicyclo[3.3.1]nona-3,7-dien-2-ones (7)–(10) and the bicyclo[3.3.1]nona-3,6-dien-2-one (11) were synthesised and irradiated. Ketones (7), (10), and (11) were photostable and (8) and (9) only underwent equilibration by geometrical photoisomerisation. This ‘free rotor’ effect by the diene system dissipates energy and prevents other photorearrangements.
C. Lam and J. M. Mellor, J. Chem. Soc., Perkin Trans. 2, 1975, 519 DOI: 10.1039/P29750000519
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