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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
Ethyl 2-[(3-chloro-phen-yl)hydrazono]-3-oxobutanoate
Abstract:
The mol-ecule of the title oxobutanoate derivative, C(12)H(13)ClN(2)O(3), adopts a keto-hydrazo tautomeric form and is roughly planar, the angle between the benzene ring and the mean plane through the hydrazone and aliphatic chain being 1.49 (6)°. This planarity is further aided by the formation of an intra-molecular N-H⋯O hydrogen bond which generates an S(6) ring motif. The aromatic ring and aliphatic chain have a trans configuration with respect to the N-N bond. In the crystal packing, centrosymmetric R(2) (2)(16) dimers are formed through pairs of weak C-H⋯O(3-oxo) inter-actions. These dimers are linked together through weak C-H⋯O(carboxyl-ate C=O) inter-actions into ribbons along the b-axis direction. These ribbons are stacked along the a-axis direction. The crystal also exhibits Cl⋯Cl [3.4988 (6) Å] and C⋯O [3.167 (2)-3.335 (2) Å] short contacts.
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