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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6 6 5 J = J = 9H,, 1 H }H .55, d of s e p t , ]H 9 H,, 1.2, 1 H 6 1.48, s, 6 H 6 1.83 a n d 1.72, e a c h a 3 H, d, J = 1.2 Hz 9 sion to aldehyde 3 and acetone on warming in CCI, solution (37 min half-life at 44"), and by the chemi-

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Das Oxetan (II), das durch Oxidation von Adamantylidenadamantan entsteht, ergibt bei seiner Reduktion ′mit Zn/Essigsäure das Diol (I), bei seiner Thermolyse in Acetonitril das Keton (III).