The first reported preparation (Roesch, 1915, 1917) of diphenyl ketimine salts in which hydroxy groups were 2- and 4- positions indicated that these compounds were unusually stable toward hydrolysis to the corresponding ketones and ammonium chloride. Subsequent studies (Culbertson, 1927, 1931) have suggested that the resistance of these phenolic ketimine salts toward hydrolysis was due to a ketimine-enamine tautomerism, or resonance, resulting in masking the ordinary reactivity of the imine (> N-H) group toward reaction with water.
Proceedings of the Iowa Academy of Science
©1942 Iowa Academy of Science, Inc.
Culbertson, J. B.
"Absorption Spectra of Ketimines with Reference to Ketimine-Enamine Tautomerism,"
Proceedings of the Iowa Academy of Science, 49(1), 281-282.
Available at: https://scholarworks.uni.edu/pias/vol49/iss1/38