A range of ortho-disubstituted C-aryl aldimines has been synthesized. N.m.r. spectroscopic analysis revealed a significant proportion of the Z-isomer at equilibrium in solution. The E–Z-isomer distribution is critically examined in terms of electronic, steric, and solvent effects. The effect of trace amounts of carboxylic acid on imine stereomutation is discussed.
J. Bjørgo, D. R. Boyd, C. G. Watson, W. B. Jennings and D. M. Jerina, J. Chem. Soc., Perkin Trans. 2, 1974, 1081 DOI: 10.1039/P29740001081
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