Original scientific paper

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

Kata Mlinarić-Majerski ; Ruđer Bošković Institute, P.O. Box 1016, 41001 Zagreb, Croatia
Dražen Pavlović ; Ruđer Bošković Institute, P.O. Box 1016, 41001 Zagreb, Croatia
Jelena Veljković ; Ruđer Bošković Institute, P.O. Box 1016, 41001 Zagreb, Croatia
Marija Šindler-Kulyk ; Ruđer Bošković Institute, P.O. Box 1016, 41001 Zagreb, Croatia

Abstract

The photochemistry of 4-methylene-2-adamantanone (1) was studied in different solvents and under direct and sensitized irradiation. Depending on the conditions, /3,y-unsaturated ketone 1 underwent reactions characteristic of isolated ketones or alkenes. Direct irradiation of 1 in benzene afforded a mixture of 2-methylenenoradamantane (11) and 4-methylenebicyclo[3.3.1]- non-2-en-7-carbaldehyde (12). Irradiation of 1 in benzene in the presence of henzophenone gave oxetanes 10, while the major products in acetone sensitized photolysis were identified as syn- and anfž-4-(3-oxobutyl)-2-adaman- tanones (8). In protic solvent (ethanol), 1 reacted smoothly to give ketal 13. The photochemical reactions that proceed through intramolecular interactions were not observed.

Keywords

Hrčak ID:

137071

URI

https://hrcak.srce.hr/137071

Publication date:

1.7.1993.

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