The reactions of base sensitive acetal X under alkaline conditions were studied. The decomposition of X depends on the OH- concentration. At low [OH-]≦10-3 M, X transforms into I, while at [OH-]=10-2 M, it decomposes to V via an enol-enolate equilibrium (IV⇌VI). These unusual base-catalyzed transformations are explained by the high mobility of the α-proton of X, and by the stability of I towards nucleophilic reagents.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry