engleski

Photochemical Behaviour of 4-Methylene-2-adamantanone, an Exocyclic β , γ - Unsaturated Ketone

The photochemistry of 4-methylene-2-adamantone (1) was studied in different solvents and under direct and sensitized irradiation. Depending in the conditions, β , γ -Unsaturated ketone 1 underwent reactions characteristic of isolated ketones or alkenes. Direct radiation of 1 in benzene afforded a mixture of 2-methylenenoradamantane (11) and 4-methylenebicyclo{; 3.3.1};-non-2-en-7-carbaldehid (12). Irradiation of 1 in benzene in presence of benzophenone gave oxetanes 10, while the major products in acetone sensitized photolysis were indentified as syn- and anti-4-(3-oxybutil)-2-adamantanones (8). In protic solvent (ethanol) , 1 reacted smoothly to give ketal 13. The photochemical reactions that proceed through intramolecular interactions were not observed.

β, γ -unsaturated ketone ; photochemistry ; oxa-di-pi-methane rearrangement

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