Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 17, Issue -, Pages 283-292Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.17.27
Keywords
Diels-Alder reaction; fluorine; nitrostyrene; norbornene; stereochemistry
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Funding
- RFBR [20-3370132]
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The Diels-Alder reaction of beta-fluoro-beta-nitrostyrenes with cyclic 1,3-dienes was studied, leading to the synthesis of a series of novel monofluorinated norbornenes with yields up to 97%. Activation parameters were calculated using kinetic data from reactions with 1,3-cyclopentadiene and 1,3-cyclohexadiene, demonstrating the synthetic utility of the cycloadducts obtained.
The Diels-Alder reaction of beta-fluoro-beta-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.
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