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RESEARCH PRODUCT

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

Sema L. IoffeAlexander S. AldoshinSavva A. PonomarevJonathan GroßValentine G. NenajdenkoTill OpatzRoman V. LarkovichAndrey A. Tabolin

subject

nitrostyreneBicyclic moleculeChemistryOrganic Chemistrystereochemistrychemistry.chemical_elementnorborneneMedicinal chemistryFull Research Paperlcsh:QD241-441Chemistrychemistry.chemical_compoundlcsh:Organic chemistryDiels–Alder reactionfluorineYield (chemistry)Fluorinelcsh:Qlcsh:ScienceNorborneneDiels–Alder reaction

description

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.

yearjournalcountryeditionlanguage
2021-01-27Beilstein Journal of Organic Chemistry
https://doi.org/10.3762/bjoc.17.27