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Updated: Jun 1, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
8-[(1E)-1-(2-Aminophenyl-iminio)eth-yl]-2-oxo-2H-chromen-7-olate
Abstract:
The title Schiff base, C(17)H(14)N(2)O(3), exists as an NH tautomer with the H atom of the phenol group transferred to the imine N atom. The iminium H atom is involved in a strong intra-molecular N(+)-H⋯O(-) hydrogen bond to the phenolate O atom, forming an S(6) motif. In the crystal structure, N-H⋯O hydrogen bonds form a C(9) chain parallel to [100] and a C(11) chain parallel to [010], while C-H⋯O hydrogen bonds form a C(11) chain parallel to [010]. The combination of N-H⋯O and C-H⋯O hydrogen bonds generates R(4) (3)(30) rings parallel to the ab plane.
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