A DFT study of the Boulton-Katritzky rearrangement of (5R)-4-nitrosobenz[c]isoxazole and its anion: pseudopericyclic reactions with aromatic transition states |
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| Authors: | Peña-Gallego Angeles Rodríguez-Otero Jesús Cabaleiro-Lago Enrique M |
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| Institution: | Departamento de Química Física, Facultade de Química, Universidade de Santiago de Compostela, Avda das Ciencias s/n. 15782, Santiago de Compostela, Spain. |
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| Abstract: | The nature of the Boulton-Katritzky rearrangement of (5R)-4-nitrosobenzc]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. |
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