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Updated: May 3, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
(E)-N,N-Diethyl-2,6-diisopropyl-4-[2-(4-nitro-phen-yl)ethen-yl]aniline
Christoph Wink1, Dieter Schollmeyer1, Heiner Detert1
1University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany.
Abstract:
The title compound, C24H32N2O2, was prepared by Horner olefination of 4-di-ethyl-amino-3,5-diiso-propyl-benzaldehyde and diethyl p-nitro-benzyl-phospho-nate. There are two independent mol-ecules (A and B) in the asymmetric unit. Their main axes, defined by the line connecting the N atoms of the nitro and amino groups, open an angle of 79.42 (3)°. Steric hindrance around the amino group is reflected in a long aryl C-N bond [1.434 (3) Å for mol-ecule A and 1.440 (3) Å for mol-ecule B], a pyramidal geometry [angle sum = 350.0 (2)° for mol-ecule A and 349.6 (2)° for mol-ecule B], and dihedral angles between the phenyl-ene group and the plane defined by the CH2-N-CH2 unit of 86.9 (3)° for mol-ecule A and 88.3 (3)° for mol-ecule B. This gives structural support for the electronic decoupling of the amino group from the nearly planar nitro-stilbene moiety (r.m.s. deviation for C, N and O atoms = 0.097 for mol-ecule A and 0.107 Å for mol-ecule B).
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