Rates and equilibria of keto–enol and–enolate ion interconversion in the 2, 4, 6-trimethylacetophenone system. Reinvestigation of the unusual bromination reaction

AJ Kresge, NP Schepp

Index: Kresge, A. J.; Schepp, N. P. Journal of the Chemical Society, Chemical Communications, 1989 , # 20 p. 1548 - 1549

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Abstract

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 themodynamic characteristics 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 ...