Journal of the Chemical Society. Chemical communications p. 232 - 233 (1986)
Update date:2022-08-10
Topics:
Ounsworth, Jim
Scheffer, John R.
Irradiation of 4-oxo-4-phenylbutanal (1) leads, via intramolecular abstraction of the aldehydic γ-hydrogen atom, to mixtures of acetophenone and 2-hydroxy-2-phenylcyclobutanone (2), and an abstraction rate constant of 8 +/- 1E8 s-1, equal to the highest rate constant so far measured for a γ-substitued butyrophenone derivative has been obtained in steady state triplet quenching studies; the high reactivity of aldehydic hydrogen atoms toward abstraction is indicated further by an approximately 2:1 δ(aldehydic) : γ(methylene) abstraction preference in the case of the homologous compound 5-oxo-5-phenylpentanal (3), which affords 2-hydroxy-2-phenylcyclopentanone (4) as the major photoproduct.
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