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

doi:10.3762/bjoc.17.27

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

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

Authors

Savva A Ponomarev¹, Roman V Larkovich¹, Alexander S Aldoshin¹, Andrey A Tabolin², Sema L Ioffe², Jonathan Groß³, Till Opatz³, Valentine G Nenajdenko¹

Affiliations

¹ Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1, Moscow, 119991, Russian Federation.
² N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences Leninsky prosp. 47, Moscow 119991, Russian Federation.
³ Department of Chemistry Johannes Gutenberg-University, Duesbergweg 10-14, D-55128 Mainz, Germany.

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.

Keywords: Diels–Alder reaction; fluorine; nitrostyrene; norbornene; stereochemistry.

Grants and funding

This work was supported by RFBR, project number 20-33-70132.