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Updated: Jun 2, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Methyl (2Z)-3-[(4-nitro-phen-yl)carbamo-yl]prop-2-enoate
Abstract:
In the title compound, C(11)H(10)N(2)O(5), the amide group is nearly coplanar and the ester group approximately perpendicular to the vinyl C-HC=CH-C group [dihedral angles of 5.0 (2) and 88.89 (5)°, respectively]. This results in a short intra-molecular O =C⋯O=C contact of 2.7201 (17) Å between the amide O atom and the ester carbonyl C atom. The prop-2-enamide fragment and the nitro group make dihedral angles of 20.42 (6) and 13.54 (17)°, respectively, with the benzene ring. An intra-molecular C-H⋯O inter-action between the benzene ring and the amide group generates an S(6) ring motif. Inter-molecular C-H⋯O and N-H⋯O hydrogen bonds complete R(2) (2)(11) ring motifs and join mol-ecules into [100] chains.
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Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
Carbocations

