Journal of the American Chemical Society p. 455 - 459 (1985)
Update date:2022-08-16
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Tee, Oswald S.
Iyengar, N. Rani
Transient 4-bromo-2,5-cyclohexadienone intermediates have been observed during the aqueous bromination of phenol and several methylated derivatives.They enolize to the corresponding p-bromophenols by both acid-catalyzed and water-catalyzed pathways in the pH range 0-6.Studies carried out in buffers also indicate both general acid catalysis (α ca 0.0) and general base catalysis (β=0.54).The latter is ascribed to simple rate-limiting proton abstraction, but the former is not so easily rationalized.The very low α is attributed to a termolecular transition state (water, substrate, and general acid) in which the dienone becomes more anion-like than cation like.This seemingly anomalous behaviour can be explained by the very large enol/keto ratio (ca. 1011) for phenol.
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