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Photolysis of the unsaturated enones 1 yields [2 + 21 cycloaddition products 2 and 3 with varying regioselectivity. Under electron-transfer conditions (PET) spirocyclic products 4 are formed. The straight [2 + 2 1 cycloaddition products 2b.c.f are converted to the spirocyclic products 4b,c,f under the same reaction conditions. The cyclobutane 5 and the cyclopropane 11 also undergo this new reductive ring opening reaction, while the stabilized system 7 is converted to reduced ringenlarged triquinane 10 which may be interesting in natural product synthesis. -Irradiation of 2-cyclohexen-1-one (14) in the presence of N,N-dimethylallylamine (15) leads to the decahydroisoquinoline 18. A mechanism involving radical intermediates is discussed. On the other hand, radical reactions have been used for reductive ring opening processes of strained systems[91 leading yields We to now new medium-sized report spirocyclic on the rings. compounds["', cyclization of olefinic and on enones, the reductive which % % % ring opening of strained systems, both induced by photoinduced electron transfer (PET). Chem. Unsaturated Enones

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