BECAS
SONZOGNI Ana SofÍa
artículos
Título:
Polar diels-alder reactions developed in a protic ionic liquid: 3-nitroindole as dienophile. theoretical studies using dft methods.
Autor/es:
CLAUDIA D. D. ROSA; CARLA M. ORMACHEA; ANA S. SONZOGNI; MARIA N. KNEETEMAN; LUIS R. DOMINGO; PEDRO M. E. MANCINI
Revista:
LETTERS IN ORGANIC CHEMISTRY
Editorial:
BENTHAM SCIENCE PUBL LTD
Referencias:
Lugar: Oak Park; Año: 2012 vol. 9 p. 691 - 695
ISSN:
1570-1786
Resumen:
N-Tosyl-3-nitroindole reacts with moderate and strong nucleophilic dienes in a polar Diels-Alder reaction using [HMIM][BF4] as a protic ionic liquid (PIL) as reaction media. In the cases in which the diene has oxygenated substituents, the PIL favors the aromatization of the formal [4+2] cycloadducts. Although the presence of the PIL in the reactions of N-tosyl-3-nitroindole as electrophile shows a clear tendency to the aromatization of the [4+2] cycloadducts, we do not note that the neoteric solvent increases the yields in relation with a molecular solvent. Part of this work is specifically concerned with theoretical studies using DFT reactivity indices. The global and local electrophilicity and nucleophilicity indices were calculated for N-tosyl-3-nitroindol and the dienes used in this study. For the studied reactions, the regioselectivity involved in the polar Diels-Alder reaction is well predicted.
