Acid and base catalysis of the mutarotation of D-arabinose oxime
Abstract
Tha mutarotation of Z-D-arabinose oxime is subject to general acid and to specific base catalysis and is proposed to proceed by an addition–elimination pathway involving cyclic N-arabinosylhydroxylamine intermediates. It is suggested that general acid catalysis (Brönsted α 0.54) proceeds via a prior equilibrium proton transfer followed by a rate-determining reaction with conjugate base.