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Diels-Alder Reaction of β-Fluoro-β-nitrostyrenes with Cyclic Dienes
preprintsubmitted on 01.12.2020, 14:49 and posted on 02.12.2020, 11:52 by Savva A. Ponomarev, Roman V. Larkovich, Alexander S. Aldoshin, Andrey A. Tabolin, Sema L. Ioffe, Jonathan Groß, Till Opatz, Valentine Nenajdenko
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 reaction with cyclopentadiene and cyclohexadiene-1,3 were used to calculate activation parameters. Furthermore, the synthetic utility of the cycloadducts obtained was demonstrated.