A DFT study of the Boulton-Katritzky rearrangement of (5R)-4-nitrosobenz[c]isoxazole and its anion: pseudopericyclic reactions with aromatic transition states.
The nature of the Boulton-Katritzky rearrangement of (5R)-4-nitrosobenz[c]isoxazole and its anion was studied employing three methodologies: calculation of magnetic properties (magnetic susceptibility, magnetic susceptibility anisotropy, and the nucleus-independent chemical shifts), the natural bonding orbital analysis, and the ACID (anisotropy of the current-induced density) method. The deep analysis of the results indicates a pseudopericyclic character for these reactions despite the aromaticity of the transition states.
Departamento de Química Física, Facultade de Química, Universidade de Santiago de Compostela, Avda das Ciencias s/n. 15782, Santiago de Compostela, Spain.
Angeles
A
Peña-Gallego
Jesús
J
Rodríguez-Otero
Enrique M
EM
Cabaleiro-Lago