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

ABSTRACT: The Diels-Alder reaction of ?-fluoro-?-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.

SUBMITTER: Ponomarev SA 

PROVIDER: S-EPMC7849230 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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

Ponomarev Savva A SA   Larkovich Roman V RV   Aldoshin Alexander S AS   Tabolin Andrey A AA   Ioffe Sema L SL   Groß Jonathan J   Opatz Till T   Nenajdenko Valentine G VG  

Beilstein journal of organic chemistry 20210127

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. ...[more]

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