Abstract
The chemical behavior of bis(trifluoromethyl)-2-azabicyclo[2.2.1]hept-5-enes and -heptanes in electrophilic addition reactions to the C-C bond, N-substitution, isomerization, and hydrogenation reactions was studied. In the reactions with soft electrophiles, cis(exo) addition of the reagent to the double bond of bis(trifluoromethyl)-2-azabicyclo[2.2.1]hept-5-ene occurred. Addition of strong electrophiles (halogens) proceeded stereospecifically and accompanied with the Wagner—Meerwein rearrangement; the reactions with harder electrophiles resulted in isomerization of the bicyclic core to give regioisomers. 3,3-Di(trifluoromethyl)-substituted 2-azanorbornenes and 2-azanorbornanes did not participate in the N-substitution reactions with electrophilic, alkylating, and acylating reagents. The possibility to hydrogenate bis(trifluoromethyl)-2-azabicyclo[2.2.1]-hept-5-enes over the Raney nickel catalyst was demonstrated.
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No human or animal subjects were used in this research.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 5, pp. 1233–1239, May, 2023.
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Khokhlov, S.S., Kutkin, A.V. Reactions of bis(trifluoromethyl)-substituted 2-azanorbornenes and 2-azanorbornanes: electrophilic addition, N-substitution, and hydrogenation. Russ Chem Bull 72, 1233–1239 (2023). https://doi.org/10.1007/s11172-023-3894-y
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DOI: https://doi.org/10.1007/s11172-023-3894-y