Computational and experimental studies on the hetero-Diels-Alder reactions of cross-conjugated enaminones with sulphene
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.
| Main Authors: | , , |
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| Format: | Digital revista |
| Language: | English |
| Published: |
The South African Chemical Institute
2009
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| Online Access: | http://www.scielo.org.za/scielo.php?script=sci_arttext&pid=S0379-43502009000100009 |
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