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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]

PMID: 33564337

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