Unusual Rearrangement of a 1,8-Naphthalene Derivative
The steric strain between nitro and carboxylic acid groups in an 8-nitro-1-naphthoic acid derivative is able to unexpectedly disrupt the aromaticity of the naphthalene core under mild reaction conditions. The addition of H<sub>2</sub>O to the aromatic ring of a highly strained naphtho oxazinium intermediate induces the fragmentation of a Csp<sup>2</sup>-Csp<sup>2</sup> bond, with a concomitant rearrangement to yield a conjugated aldehyde. Key intermediates have been characterized, and the X-ray structure of the derivative has been obtained. Density functional theory (DFT) studies were performed to confirm the proposed mechanism.
Authors
- Joaquin Rodriguez Moran (ORCID: https://orcid.org/0000-0002-1925-986X)
- Angel Luis Fuentes de Arriba (ORCID: https://orcid.org/0000-0001-7424-8146)
- Irene Boya del Teso (ORCID: https://orcid.org/0000-0001-5446-4685)
- José J. Garrido‐González (ORCID: https://orcid.org/0000-0001-7696-7902)
- Asmaa Habib
- Luis Simón (ORCID: https://orcid.org/0000-0002-3781-0803)
- Estela Sánchez‐Santos (ORCID: https://orcid.org/0000-0001-7129-4622)
- Francisca Sanz B
Institutions
- Universidad de Salamanca (ES)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-04-03
- DOI
- https://doi.org/10.1021/acs.joc.5c00021
- Citations
- 1
- Primary Topic
- Coordination Chemistry and Organometallics
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Ministerio de Ciencia, Innovación y Universidades
- Ministerio de Educación y Formación Profesional