Journal of Organic Chemistry p. 89 - 92 (1990)
Update date:2022-08-03
Topics:
Netto-Ferreira, J.C.
Avellar, I.G.J.
Scaiano, J.C.
The photochemistry of a series of 10 α-(aryloxy)acetophenones has been examined by quantum yield, product studies, and laser flash photolysis techniques.Triplet decay involves a competition of β-cleavage with intramolecular quenching by the β-aryl group, the latter being favored in all systems.Typical triplet lifetimes at room temperature range from 60 to 260 ps and are rather insensitive to the substitution pattern. β-Cleavage rate constants range between 1*107 and 3*109 s-1 and are strongly favored by electron releasing substituents, such as 4-methoxy.The determination of true quantum yields of β-cleavage requires the addition of thiophenol as a radical trap to prevent the efficient back reaction that takes place otherwise; under these conditions quantum yields range from 10-3 to 0.14, the highest value being obtained for the 4-methoxy and 4-hydroxy derivatives.
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