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Updated: May 13, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
(2E)-1-(2-Methyl-4-phenyl-quinolin-3-yl)-3-(3-methyl-thio-phen-2-yl)prop-2-en-1-one
R Prasath1, P Bhavana, Seik Weng Ng
1Department of Chemistry, BITS, Pilani-K. K. Birla Goa Campus, Goa 403 726, India.
Abstract:
In the title compound, C24H19NOS, the quinoline residue (r.m.s. deviation = 0.018 Å) is essentially orthogonal to both the phenyl [dihedral angle = 88.95 (8)°] and 2-thienyl [81.98 (9)°] rings. The carbonyl O atom lies to one side of the quinoline plane, the carbonyl C atom is almost coplanar and the remaining atoms of the chalcone residue lies to the other side, so that overall the mol-ecule has an L-shape. The conformation about the ethyl-ene bond [1.340 (2) Å] is E. In the crystal, a supra-molecular chain with the shape of a square rod aligned along the b-axis direction is sustained by C-H⋯π inter-actions, the π-systems being the heterocyclic rings.
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