Diets-Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes

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.

Automated summary

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.