6533b85afe1ef96bd12ba058

RESEARCH PRODUCT

Nitropyrroles, Diels-Alder reactions assisted by microwave irradiation and solvent effect. An experimental and theoretical study

Pedro ManciniMaria KneetemanMauro CainelliCarla OrmacheaLuis R. Domingo

subject

MOLECULAR ELECTRON DENSITY THEORY010402 general chemistryPhotochemistrySOLVENT EFFECTS01 natural sciencesAnalytical ChemistryInorganic Chemistrychemistry.chemical_compoundNucleophileMICROWAVEPOLAR DIELS-ALDERSpectroscopyNITROPYRROLES010405 organic chemistryOtras Ciencias QuímicasOrganic ChemistryCiencias QuímicasToluene0104 chemical sciencesSolventchemistryIonic liquidElectrophilePolarSolvent effectsCIENCIAS NATURALES Y EXACTASMicrowave

description

The behaviors of N-tosylnitropyrroles acting as electrophilic dienophiles in polar Diels-Alder reactions joint to different dienes of increeased nucleophilicity are analyzed. The reactions were developed under microwave irradiation using toluene or protic ionic liquids (PILs) as solvents and in free solvent conditions. In all the cases explored we observed good yields in short reaction times. For these reactions, the free solvent condition and the use of protic ionic liquids as solvents offer similar results. However, the free solvent conditions favor environmental sustainability. The role of PILs in these polar Diels-Alder reactions has been theoretically studied within the Molecular Electron Density Theory. Fil: Mancini, Pedro Maximo Emilio. Universidad Nacional del Litoral. Instituto de Química Aplicada del Litoral. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Química Aplicada del Litoral.; Argentina Fil: Kneeteman, Maria Nelida. Universidad Nacional del Litoral. Instituto de Química Aplicada del Litoral. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Química Aplicada del Litoral.; Argentina Fil: Cainelli, Mauro. Universidad Nacional del Litoral. Instituto de Química Aplicada del Litoral. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Química Aplicada del Litoral.; Argentina Fil: Ormachea, Carla. Universidad Nacional del Litoral. Instituto de Química Aplicada del Litoral. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Química Aplicada del Litoral.; Argentina Fil: Domingo, Luis R.. Universidad de Valencia; España

yearjournalcountryeditionlanguage
2017-11-01Journal of Molecular Structure
https://doi.org/10.1016/j.molstruc.2017.06.109