Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes
Savva A. Ponomarev, Roman V. Larkovich, Alexander S. Aldoshin, Andrey A. Tabolin, Sema L. Ioffe, Jonathan Groß, Till Opatz, Valentine G. Nenajdenko
Abstract
The Diels-Alder reaction of β-fluoro-β-nitrostyrenes with cyclic 1,3-dienes was investigated. A series of novel monofluorinated norbornenes was prepared in up to 97% yield. The reaction with 1,3-cyclohexadiene permits the preparation of monofluorinated bicyclo[2.2.2]oct-2-enes. The kinetic data of the reactions with 1,3-cyclopentadiene and 1,3-cyclohexadiene were used to calculate activation parameters. Furthermore, the synthetic utility of the cycloadducts obtained was demonstrated.
Topics & Concepts
CyclopentadieneChemistryYield (engineering)Diels–Alder reactionBicyclic moleculeOrganic chemistryPericyclic reactionMedicinal chemistryComputational chemistryCatalysisMetallurgyMaterials scienceFluorine in Organic ChemistryOxidative Organic Chemistry ReactionsAsymmetric Synthesis and Catalysis