The ketene derived products and unsaturated aldehydes produced upon solution photolysis of a series of bicyclooctanones (bicyclo [2.2. 2] octan-2-one (1), bicyclo [3.2. 1] octan-2-one (6), l, 8, 8-trimethylbicyclo [3.2. 1] octan-2-one (12)) are reported. Estimated strain energies of the approximate transition states involved and conformational analysis are utilized as guides to rationalize the results. This approach should assist more accurate predictions of ...