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

Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes Full article

Journal

Beilstein Journal of Organic Chemistry
ISSN: 2195-951X , E-ISSN: 1860-5397

Output data

Year: 2021, Volume: 17, Pages: 283-292 Pages count : 10 DOI: 10.3762/bjoc.17.27

Authors

Ponomarev Savva A ¹ , Larkovich Roman V ¹ , Aldoshin Alexander S ¹ , Tabolin Andrey A ² , Ioffe Sema L ² , Groß Jonathan ³ , Opatz Till ³ , Nenajdenko Valentine G ¹

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 and
3	Department of Chemistry Johannes Gutenberg-University, Duesbergweg 10-14, D-55128 Mainz, Germany

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.

Ponomarev S.A. , Larkovich R.V. , Aldoshin A.S. , Tabolin A.A. , Ioffe S.L. , Groß J. , Opatz T. , Nenajdenko V.G.
Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes
Beilstein Journal of Organic Chemistry. 2021. V.17. P.283-292. DOI: 10.3762/bjoc.17.27 WOS Scopus OpenAlex

≡ Web of science:	WOS:000614166700002
≡ Scopus:	2-s2.0-85101352973
≡ OpenAlex:	W3124114046