Diels‐Alder Reaction of β‐Fluoro‐β‐nitrostyrenes. Synthesis of Mono‐fluorinated Six‐Membered Derivatives

Diels‐Alder Reaction of β‐Fluoro‐β‐nitrostyrenes. Synthesis of Mono‐fluorinated Six‐Membered Derivatives Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2020, Volume: 2020, Number: 17, Pages: 2479-2492 Pages count : 14 DOI: 10.1002/ejoc.202000054

Authors

Larkovich Roman V. ¹ , Ponomarev Savva A. ¹ , Aldoshin Alexander S. ¹ , Tabolin Andrey A. ² , Ioffe Sema L. ² , Nenajdenko Valentine G. ¹

Affiliations

1	Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1, 119991 Moscow, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russian Federation

The Diels-Alder reaction of β-fluoro-β nitrostyrenes with some linear dienes was investigated. A number of monofluorinated [4+2]-cycloadducts was prepared in up to 90 % yield. The kinetics of [4+2]-cycloaddition to 2,3-dimethyl-1,3-butadiene was studied in detail to reveal substituent effect and activation parameters of the reaction. It was demonstrated that base-induced elimination of nitrous acid followed by oxidative aromatization can be used for the preparation of mono-fluorinated biphenyls in up to 92 % isolated yield.

Larkovich R.V. , Ponomarev S.A. , Aldoshin A.S. , Tabolin A.A. , Ioffe S.L. , Nenajdenko V.G.
Diels‐Alder Reaction of β‐Fluoro‐β‐nitrostyrenes. Synthesis of Mono‐fluorinated Six‐Membered Derivatives
European Journal of Organic Chemistry. 2020. V.2020. N17. P.2479-2492. DOI: 10.1002/ejoc.202000054 WOS Scopus OpenAlex

≡ Web of science:	WOS:000530893200003
≡ Scopus:	2-s2.0-85081732388
≡ OpenAlex:	W3011341241