College of Chemistry and Chemical Engineering, Sichuan University of Arts and Science, Dazhou, 635711, People's Republic of China
*Corresponding Author E-mail: huqs@163.com
Online published on 31 January, 2014.
The mechanism of the multi-channel reaction (2E,4E)-6-hydroxyhexa-2,4-dien-1-ylium + furan-2,5-dione was investigated by density functional theory (DFT). The geometries and the frequencies of reactants, intermediates, transition states, and products were calculated at the B3LYP/6–311G(d) level. The vibration analysis and the IRC analysis demonstrated the authenticity of transition states, and the reaction processes were confirmed by the changes of charge density at bond-forming critical point. Four alternative reaction channels have been investigated. The reaction channel of producing (3aR,4S,5S,7aR)-5-methyl-3-oxo-1,3,3a,4,5,7a-hexahydroisobenzofuran-4-carboxylic acid is the major channel and the others are minor channels.
Reaction mechanism, transition states, density functional theory, multi-channel reaction
