YLURES SANS SEL, ÉVOLUTION EN PHOSPHORANES ET ÉQUILIBRE YLURE ⇄ PHOSPHORANE; INFLUENCE DES RÉACTIFS DE PIÉGEAGE: III PIÉGEAGE PROTIQUE

Abstract This work is a contribution to rationalize the trapping behaviour of the 1,3 dipolar species created by addition of methoxy tetramethyl-dioxaphospholane-1,3,2 on dimethylacetylene dicarboxylate. In the past, we have given examples with protic reagents (methanol, phenol, benzoic acid and phtalimid). In the present work, we study two types of protic reagents; one type belongs to the family of carboxylic acids. Five benzoic acids are tested. The other type belongs to a group of compounds (imides, amides, indole, pyrrole) bearing a N-H bond. Using the concept of hard and soft acids and bases and the symbiotic effect around phosphorus atom, the behaviour of this dipolar species is rationalized. Ce travail est une contribution a l'explication rationnelle des reactions de piegeage du zwitterion 1,3,Cree par l'addition du methoxy tetra methyl dioxaphospholanne 1,3,2 sur l'acetylene dicarboxylates de methyle. Dans le passe, nous avons donne des exemples de piegeage protiques (avec le methanol, le phenol, ...