Réactivité des α-halobutyrolactones à halogènes tertiaires vis-à-vis des nucléophiles faiblement basiques

J Gharbi-Benarous, MM Essayegh…

Index: Gharbi-Benarous, Josyane; Essayegh, Mounir M.; Dana, Gilbert Canadian Journal of Chemistry, 1987 , vol. 65, p. 2031 - 2038

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Citation Number: 8

Abstract

2-Methyl-4-phenylbutenolide (5) is prepared in a quantitative manner by an elimination of HBr from the corresponding bromolactones 3. This reaction, induced by halide ions at 100° C in polar aprotic solvents (DMF, DMSO), is accompanied by a bimolecular nucleophilic substitution. In these reactions, the solvent seems able to play an active role. A polar solvent induces the necessary activation of the substrate (by a prior strong polarization of the C-Br ...