South African Journal of Chemistry
On-line version ISSN 1996-840X
Print version ISSN 0379-4350
SINGH, Parvesh; BISETTY, Krishna and MAHAJAN, Mohinder P.. Computational and experimental studies on the hetero-Diels-Alder reactions of cross-conjugated enaminones with sulphene. S.Afr.j.chem. (Online) [online]. 2009, vol.62, pp.47-55. ISSN 1996-840X.
Ab initio and density functional theory (DFT) calculations have been used to investigate the feasibility of cycloaddition reactions of enaminones 1 with sulphene. Specifically, the geometry optimizations, frequency calculations and self-consistent reaction-field (SCRF) solvent simulations in combination with higher-quality relative energies carried out at the DFT level using the 6-31 + G(d) basis set suggests that the product obtained is both thermodynamically and kinetically preferred, indicating the feasibility of this reaction. Additionally, experimental studies carried out on the reactions of these enaminones 1 with sulphene were also found to be in agreement with the theoretical predictions resulting in the synthesis of a variety of novel oxathiine derivatives having great biological and medicinal importance.
Keywords : Enaminones; cycloadditions; sulphene; DFT; SCRF.