Journal of the Chemical Society. Perkin transactions II p. 1343 - 1349 (1983)
Update date:2022-08-04
Topics:
Verheijdt, Paul L.
Cerfontain, Hans
The photoaddition of five non-enolizing 1,2-diketones (1a-e), bipivaloyl, and biacetyl to various simple alkenes has been investigated.The dihidrodioxine formation dominates over the formation of oxetane, α-keto allylic ether, and 1,2-adduct (α-hydroxyketone) for three cyclic 1,2-diketones (1b-d) that have a syn-periplanar (lowest) excited 1,2-diketo configuration.The four-membered ring diketone (1a) photo-fragments prior to its addition to the alkene.Biacetyl with an anti-periplanar excited 1,2-diketo configuration does not form dihydrodioxines.No information on the geometry of the excited 1,2-diketo configuration could be obtained with (1e) and (2), as the rate of α-cleavage
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