The reactions leading to the Diels-Alder adducts of protoanemonin (5-methylene-2(5H)-furanone) with three unsymmetrical dienes isoprene, trans-piperylene ((E)-1,3-pentadiene), and (E)-2-methyl-1,3-pentadiene have been studied using the AM 1 molecular orbital method at both the RHF and open shell (3 × 3CI) levels. The results suggest that the reactions take place via very unsymmetrical transition states or similar biradicals. The regiospecificity of the dienes is well explained by the open shell calculations and is in reasonable agreement with the RHF calculations. © 1993.
|Journal||Journal of Molecular Structure: THEOCHEM|
|Publication status||Published - 1 Jan 1993|