Abstract
The mode of singlet oxygen attack on norbornene derivatives was probed via a study of the dye-sensitized photooxygenation of 2-ethylidenebicyclo[2.2.1]hept-5-ene ( 1). Reduction of the resulting allylic hydroperoxides provided the epimeric 2-hydroxy-2-vinylbicyclo[2.2.1]hept-5-enes ( 2 and 3) and 2-(1-hydroxyethyl)bicyclo[2.2.1]hept-2,5-diene ( 4), the relative yields of which were apparently controlled by steric factors. Also isolated were two novel multicyclic ketones, 5 and 6, derived from thermal rearrangements of the primary oxidation products.
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