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Updated: May 14, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
endo,endo-Tetra-cyclo-[6.2.1.1(3,6).0(2,7)]dodeca-9-en-anti-11-yl 4-bromo-benzoate
Barry A Lloyd1, Atta M Arif, Robert J Coots
1Chemistry Department, Weber State University, Ogden, Utah 84408-2503, USA.
Abstract:
The title compound 1-OPBB, C(19)H(19)BrO(2), contains a dechlorinated and hydrogenated isodrin backbone with an anti-4-bromo-benzoate substituent at one of the methano bridges. The dihedral angle between the CO(2) ester plane and the benzene ring plane is 8.5 (2)°. In the crystal, the ester groups stack over benzene rings: the mol-ecules pack as conformational enanti-omers, with nearest parallel benzene ring planes separated by a perpendicular distance of 3.339 (1) Å. The nearest benzene-ring centroids are 5.266 (1) Å apart. Possible structural correlation with enhanced solvolytic reactivity is investigated.
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