Abstract A series of 1, 2, 3, 4, 5, 6-hexafluorobicyclo [4.2. 0] octa-2, 4-dienes was subjected to direct irradiation with ultraviolet light and to triplet sensitization. While all of the dienes cyclized smoothly upon direct irradiation to tricyclo [4.2. 0.0 2, 5] oct-3-enes, their behavior when triplet sensitized was strongly dependent upon the substituents in the 7-and 8- positions. Responses included no reaction, cyclization to tricyclooctene, and ...