Reactions de cycloaddition dipolaire-1,3 des thiazolones mesoioniques avec des composes ethyleniques-1: Etude des problemes de stereochimie poses par l'approache dipole-dipolarophile |
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| Authors: | M. Baudy A. Robert G. Guimon |
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| Affiliation: | Groupe de Recherches de Chimie Structurale, Equipe associée au C.N.R.S., Université de Rennes, 35042 Rennes, France;Laboratoire de Chimie Organique Physique, E.R.A. 895, Université de Pau et des Pays de l''Adour, Avenue Philippon, 64000 Pau, France |
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| Abstract: | The stereochemistry of cycladducts obtained through the reaction of mesoionic thiazolones with ethylenic dipolarophiles is established. The dipole-dipolarophile approach is discussed in terms of interactions between the frontier orbitals. When the dipolarophile is acrylonitrile we note the importance of the destabilising interaction the HOMO orbitals. When the dipolarophile is vinyl ethyl ether we show that the interaction LUMO dipole-HOMO dipolarophile can be dominating. |
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