A DFT Study of the Boulton−Katritzky Rearrangement of (5R)-4-Nitrosobenz[c]isoxazole and Its Anion: Pseudopericyclic Reactions with Aromatic Transition States
- 21 September 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (21) , 7013-7017
- https://doi.org/10.1021/jo0491509
Abstract
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.This publication has 41 references indexed in Scilit:
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