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.
P. Finch and Z. M. Merchant, J. Chem. Soc., Perkin Trans. 2, 1982, 199 DOI: 10.1039/P29820000199
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