Abstract

While irradiation (350 nm) of the title cyanocyclohexenone 3a in the presence of 2,3-dimethylbut-2-ene affords hexahydroindeno-1,2-oxazole 6 selectively, photolysis of 3a in the presence of 2-methylbut-2-ene or isobutene gives mixtures of tricyclic 1,2-oxazoles and 2-oxobicyclooctane-1-carbonitriles, the product ratio oxazole/bicyclooctane decreasing with increasing I p of the alkene. The constitution of the photoproducts indicate that oxazoles and bicyclooctanes result from two isomeric triplet 1,4-biradicals, formed by addition of the less substituted C-atom of the alkene to either of the olefinic C-atoms of triplet 3a, respectively.

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