TY - JOUR A1 - Ponomarev, Savva A. A1 - Larkovich, Roman V. A1 - Aldoshin, Alexander S. A1 - Tabolin, Andrey A. A1 - Ioffe, Sema L. A1 - Groß, Jonathan A1 - Opatz, Till A1 - Nenajdenko, Valentine G. T1 - Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes JF - Beilstein Journal of Organic Chemistry PY - 2021/// VL - 17 SP - 283 EP - 292 SN - 1860-5397 DO - 10.3762/bjoc.17.27 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.17.27 KW - Diels–Alder reaction KW - fluorine KW - nitrostyrene KW - norbornene KW - stereochemistry N2 - 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. ER -