Rates and Equilibria of Keto-Enol and -Enolate Ion Interconversion in the 2,4,6-Trimethylacetophenone System. Reinvestigation of the Unusual Bromination Reaction

Article abstract of DOI:10.1039/c39890001548

The bromination of 2,4,6-trimethylacetophenone, whose unusual kinetics were once thought to be the result of slow, sterically hindered addition of bromine to the enol, was found to be a ring- rather than a side-chain-substitution reaction; kinetic and thermodynamic charactristics of this keto-enol system were determined by a combination of flash-photolytic and conventional kinetic techniques and were found to be little different from those of the parent (unsubstituted) acetophenone keto-enol system.