Abstract
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.
Highlights
Organofluorine compounds play an exceptionally important role in various fields of science and technology
It should be noted that in the present work we indicate an isomer as exo or endo according to the stereo-position of the fluorine atom
Approximately a 2:1 ratio was observed for the nitro- and carboxymethyl-substituted products 3b, 3c, whereas in the absence of a Scheme 3: Diels–Alder reaction of nitrostyrenes 1 with CHD. (а) Reaction under microwave activation
Summary
Organofluorine compounds play an exceptionally important role in various fields of science and technology. Considering the high interest in such structures and the unique role of fluorine, we believe that novel norbornene derivatives obtained in the framework of this study can become relevant compounds in practical use. We studied the Diels–Alder reaction of β-fluoro-βnitrostyrenes 1 with 1,3-cyclopentadiene (CPD) to prepare a series of novel monofluorinated norbornenes.
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