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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
4-[(4-Methyl-phen-yl)amino]-pent-3-en-2-one
Gertruida J S Venter1, Gideon Steyl, Andreas Roodt
1Department of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa.
Abstract:
The title enamino-ketone, C(12)H(15)NO, is a derivative of 4-(phenyl-amino)-pent-3-en-2-one with an approximately planar pentenone backbone, the greatest displacement from the plane being 0.042 (1) Å; the asymmetry in C-C distances in the group suggests the presence of unsaturated bonds. The dihedral angle between the benzene ring and the pentenone plane is 29.90 (4)°. In the crystal, an intra-molecular N-H⋯O inter-action and an inter-molecular C-H⋯O hydrogen bond are observed.
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