Abstract The nature of the photochemical carbon-halogen bond cleavage in α-halo cycloalkanones depends on the halogen atom bonded and on the ring size of the cycloalkanone. In the 2-halo-1-indanone series the amount of radical products increased from iodine to chlorine, while in the case of 2-halo-3, 4-dihydro-1 (2H)-naphthalenone 43% for iodo, 32% for bromo, and 53% for the chloro derivative were found. On the other hand, ...