The thermolysis of adamantylideneadamantane dioxetane 1 was investigated. The activation energy for cleavage of 1 was found to be ca. 37 kcal/mol and essentially solvent independent. The thermal decomposition of 1 is chemiluminescent. The yield and nature of the chemically produced excited states were determined by chemical titration and found to be ca. 2% singlet and ca. 15% triplet. Photolysis of 1 leads to the adiabatic formation of singlet and triplet adamantanone with yields of 8 and 40%, respectively. A detailed kinetic analysis of the photochemical reactions of adamantanone with frarw-dicyanoethy-

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