The mechanism of the isomerization of the enol acetate of 2-aceto-1,3-cyclohexanedione has been discussed in detail. The possible 1,3-H and 1,5-H shifts in isomerization were investigated systematically. It seems that this mechanism includes two successive 1,5-sigmatropic shifts, i.e. 1,5-acetyl and 1,5-H shifts. Density functional theory calculations have been performed to evaluate the reasonability of the proposed mechanisms. The effect of the solvent upon the rate-determining steps has been also considered. In addition, the relative stabilities of the reactant, the product as well as the intermediates in the proposed mechanism have been examined and discussed.

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Volume27, Issue6

June, 2009

Pages 1132-1136

Computational Investigation of 1,3-H and 1,5-H Shifts in Isomerization of Enol Acetate of 2-Aceto-1,3-cyclohexanedione

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Computational Investigation of 1,3-H and 1,5-H Shifts in Isomerization of Enol Acetate of 2-Aceto-1,3-cyclohexanedione

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