Judicious choice of precipitation conditions can lead to self-sorting of equilibrating mixtures of aromatic aldehydes and substituted anilines into a handful of imine products. The selectivity of this process is caused by the solubility differences among possible imines in the EtOH–H2O solvent mixtures used in precipitation.
R. C. Lirag, K. Osowska and O. Š. Miljanić, Org. Biomol. Chem., 2012, 10, 4847 DOI: 10.1039/C2OB25736J
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