A Theoretical Study of 2-nitrofuran vs 3-nitrofuran as Dienophilic Electrophile in Polar Cycloaddition Reaction: Comparison of the Reactivity and Reaction Mechanism
Mauro Cainelli
Laboratorio Fester, Química Orgánica, IQAL (UNL-CONICET), Facultad de Ingeniería Química, Santa Fe, Argentina
Carla M. Ormachea
Laboratorio Fester, Química Orgánica, IQAL (UNL-CONICET), Facultad de Ingeniería Química, Santa Fe, Argentina
Pedro M. E. Mancini
Laboratorio Fester, Química Orgánica, IQAL (UNL-CONICET), Facultad de Ingeniería Química, Santa Fe, Argentina
María N. Kneeteman *
Laboratorio Fester, Química Orgánica, IQAL (UNL-CONICET), Facultad de Ingeniería Química, Santa Fe, Argentina
*Author to whom correspondence should be addressed.
Abstract
In this study, we analyzed in a theoretical form the behavior of 2-nitrofuran and 3-nitrofuran acting as dienophilic electrophiles in polar cycloaddition reactions joint to different dienes. The reactivity and regioselectivity was discussed employing global and local reactivity indexes, respectively The reaction mechanisms of these cycloadditions were compared through the transition state structures and energies calculated.
Keywords: 2-nitrofuran, DFT, mechanism, cycloaddition reaction