EFFET DE SOLVANT SUR SUPPORT SOLIDE: COMPARAISON DE POLYMERES PORTEURS DE MOTIFS HEXAMETHYLPHOSPHOROTRIAMIDE, N-PYRROLIDONE ET N-OXAZOLIDINONE SUR L'ALKYLATION DE L'ENOLATE DE L'ACETYLACETATE D'ETHYLE

Article abstract of DOI:10.1016/0040-4020(82)85033-3

The rate of ethylation by Et2SO4 of potassium enolate of ethylacetoacetate is enhanced in the presence of polymers bearing N-pyrrolidone (P-N.P.) or N-oxazolidone (P-N.O.) moieties.It depends inter alia on the nature of the polymeric skeleton.The C/O alkylation as well as the ratio E/Z of the enol ethers gives an account of the interaction of the enolate with its associated cation inside the polymer: the efficiency is thus: P-HMPA > P-N.P. > P-N.O., although a different order is observed on the reaction rate: P-HMPA > P-N.O. > P-N.P..Thus, this test reaction gives more information on the different interactions involved than the study of rate enhancements of nucleophilic substitutions.