REACTIONS DE CYCLOADDITION DIPOLAIRE-1,3 DES THIAZOLONES MESOIONIQUES AVEC DES COMPOSES ETHYLENIQUES-1. ETUDE DES PROBLEMES DE STEREOCHIMIE POSES PAR L'APPROCHE DIPOLE-DIPOLAROPHILE

Article abstract of DOI:10.1016/0040-4020(82)85110-7

The stereochemistry of cycloadducts 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 between the HOMO orbitals of the reactants.When the dipolarophile is vinyl ethyl ether we show that the interaction LUMO dipole-HOMO dipolarophile can be dominating.