Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 1132-1136 |
| Number of pages | 5 |
| Journal | Chinese Journal of Chemistry |
| Volume | 27 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - Jun 2009 |
| Externally published | Yes |
Keywords
- 2-aceto-1,3-cyclohexanedione
- Density functional theory
- Hydrogen shift
- Isomerization mechanism
- Solvent effect