Unusual reactivities of acridine derivatives in catalytic hydrogenation. A combined experimental and theoretical study

Abstract : Hydrogenation of acridine derivatives over Rh/Al2O3, has been studied. Strong influence of the pyrrolidino-substituent on the reduction pathway and reductions products was found. When, the reaction was performed on the unsubstituted acridine nucleus full conversion was obtained in 8 h. Under the same conditions, when a pyrrolidine substituent was settled on the central ring of acridine (9-position), a pure product was obtained with the two lateral carbocycles reduced whereas the central heterocyclic ring was not reduced. When the pyrrolidin e substituent was at the 1-position, pure partially reduced central heterocyclic ring was obtained, but the compound was rapidly re-oxidized by air. In order to clarify such substituent effect, theoretical calculations were performed. Considering the energies and thermodynamic values of each intermediate and product as well as the interaction with the catalyst surface, the selectivity and diversity in the reduced product formation were partially explained and different reaction pathways were drawn according to the substitution pattern on the acridine scaffold.
Type de document :
Article dans une revue
Journal of Molecular Catalysis A: Chemical, Elsevier, 2013, 371, pp.63-69. 〈10.1016/j.molcata.2013.01.015〉
Liste complète des métadonnées

https://hal.archives-ouvertes.fr/hal-00877304
Contributeur : Agnès Bussy <>
Soumis le : lundi 28 octobre 2013 - 11:15:03
Dernière modification le : jeudi 7 février 2019 - 14:51:23

Identifiants

Citation

Pierre Mignon, Martin Tiano, Philippe Belmont, Alain Favre-Reguillon, Henry Chermette, et al.. Unusual reactivities of acridine derivatives in catalytic hydrogenation. A combined experimental and theoretical study. Journal of Molecular Catalysis A: Chemical, Elsevier, 2013, 371, pp.63-69. 〈10.1016/j.molcata.2013.01.015〉. 〈hal-00877304〉

Partager

Métriques

Consultations de la notice

232