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Updated: Jun 2, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
(E)-3-(1-Naphthyl-amino)-methyl-ene-(+)-camphor
Abstract:
In the crystal structure of the title ketoamine {systematic name: (E)-1,7,7-trimethyl-3-[(1-naphthyl-amino)-methyl-idene]bicyclo-[2.2.1]heptan-2-one}, C(21)H(23)NO, there are two independent mol-ecules in the asymmetric unit. Both mol-ecules have an E configuration about the alkene function. The main conformational difference between the mol-ecules is in the orientation of the plane of the naphthyl rings with respect to the camphor fragment. The torsion angle about the enamine C-N bond is 21.3 (7)° for mol-ecule A, but -24.4 (8)° for mol-ecule B. Inter-molecular N-H⋯O hydrogen bonds between the amino and ketone groups of adjacent independent mol-ecules sustain the crystal, and the resulting extended chains, containing an alternating sequence of the two independent mol-ecules, run parallel to the [001] direction and can be described by a graph-set motif of C(2) (2)(12).
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