REACTIONS COMPETITIVES SUR BASES SOLIDES : EFFETS DU CATION DE L'EAU

Article abstract of DOI:10.1016/S0040-4039(01)92878-3

In the presence of MOH (M=Li, Na, or K), Ph-CHCl-CO2i.Pr (1) and CH2=CHCO2t.Bu in dioxane lead to the expected formation of cyclopropyl esters and to the concurrent saponification of 1 to Ph-CHCl-COO(1-)*M(1+).The very important influence of the cation size and the smaller one of the water on the competition between the two reactions due to the basic or the nucleophilic attack of 1 by MOH is evidenced.The process can be orientated to the cyclopropanic esters formation by using dehydrated KOH.