ACTION DES COMPOSES ORGANOMAGNESIENS SUR LES PYRONES-2 - VII ETUDE DE LA STABILITE RELATIVE DES HYDROXY-6 DYHIDRO-5,6 2H-PYRANNES ET DES CETOLS TAUTOMERES CORRESPONDANTS

Article abstract of DOI:10.1016/S0040-4020(01)91804-6

In the reaction between organomagnesium compounds and 2-pyrones, the relative stability of the 6-hydroxy 5,6 2H-pyrans and their tautomeric forms (ketols) has no influence on the reaction pathway.When ethylenic ketols are obtained, the corresponding tautomeric dihydropyranols are prepared in a selective way by reaction of nucleophilic reagents on the 3,6-dihydropyrones.In the other hand, the exclusive formation either of the dihydropyranols or of the unsatured ketols E, during these two reactions, shows up that here is no equilibrium between these two entities in the experimental conditions.