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Updated: Jul 19, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
(2S,RS)-6-Phenyl-1-(p-tolylsulfinyl)hexa-3(E),5(E)-dien-2-ol
Oscar Donoso-Tauda1, Carlos A Escobar, Ramiro Araya-Maturana
1Laboratorio de Recursos Naturales, Departamento de Ciencias Químicas, Facultad de Ecología y Recursos Naturales, Universidad Nacional Andrés Bello, Avenida República 275, Santiago, Chile.
Abstract:
The molecule of the title compound, C19H20O2S, corresponds to a chiral sulfinyldienol with two stereogenic centres, viz. the C atom susbtituted by the hydroxy group and the sulfinyl S atom. The molecule displays a V-shape in the solid state. The dihedral angle defined by the least-squares planes of the aromatic rings is 72.9 (1) degrees. The packing pattern exhibits the following intermolecular hydrogen bonds: one O-H...O [H...O = 1.98 A, O...O = 2.785 (4) A and O-H...O = 166 degrees] and two C-H...O [H...O = 2.58 and 2.60 A, C...O = 3.527 (5) and 3.347 (5) A, and C-H...O = 164 and 134 degrees]. These define a chain along b.
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