β-氟-β-硝基苯乙烯与环状二烯的狄尔斯-阿尔德反应。

Diels-Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes.

作者信息

Ponomarev Savva A, Larkovich Roman V, Aldoshin Alexander S, Tabolin Andrey A, Ioffe Sema L, Groß Jonathan, Opatz Till, Nenajdenko Valentine G

机构信息

Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1, Moscow, 119991, Russian Federation.

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences Leninsky prosp. 47, Moscow 119991, Russian Federation.

出版信息

Beilstein J Org Chem. 2021 Jan 27;17:283-292. doi: 10.3762/bjoc.17.27. eCollection 2021.

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.