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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 8, Number 5
May 20, 1987 

Photochemical C4-Cycloadduct Formation between 5(E)-Styryl-1,3-dimethyluracil and Some Olefins-Via Photochemical Diels-Alder Type [4 + 2] Adduct
Sang Chul Shim*, Eun Ju Shin
The cyclobutane forming photocycloaddition reaction of 5(E)-styryl-1,3-dimethyluracil with some olefins occurs on the 5,6-double bond of uracil ring rather than the expected central double bond via an intermediate, probably the photochemical Diels-Alder type adduct. This intermediate formed on short term irradiation of 5(E)-styryl-1,3-dimethyluracil and 2,3-dimethyl-2-butene solution is converted into the C4-cycloadduct on the prolonged irradiation. Quantum yield of the intermediate formation is not linear with the concentration of 2,3-dimethyl-2-butene probably due to the secondary reaction accompanied with the complex reaction kinetics. The intermediate is formed from the lowest excited singlet state.
376 - 380
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