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Reaction Electronic Flux Perspective on the Mechanism of the Zimmerman Di-π-methane Rearrangement

Matute, Ricardo A. and Pérez, Patricia and Chamorro, Eduardo and Villegas-Escobar, Nery and Cortés-Arriagada, Diego and Herrera, Barbara and Gutiérrez-Oliva, Soledad and Toro-Labbé, Alejandro (2018) Reaction Electronic Flux Perspective on the Mechanism of the Zimmerman Di-π-methane Rearrangement. Journal of Organic Chemistry, 83 (11). pp. 5969-5974. ISSN 0022-3263. http://resolver.caltech.edu/CaltechAUTHORS:20180319-125008328

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Abstract

The reaction electronic flux (REF) offers a powerful tool in the analysis of reaction mechanisms. Noteworthy, the relationship between aromaticity and REF can eventually reveal subtle electronic events associated with reactivity in aromatic systems. In this work, this relationship was studied for the triplet Zimmerman di-π-methane rearrangement. The aromaticity loss and gain taking place during the reaction is well acquainted by the REF, thus shedding light on the electronic nature of reactions involving dibenzobarrelenes.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acs.joc.8b00499DOIArticle
https://pubs.acs.org/doi/10.1021/acs.joc.8b00499PublisherArticle
https://pubs.acs.org/doi/suppl/10.1021/acs.joc.8b00499PublisherSupporting Information
ORCID:
AuthorORCID
Matute, Ricardo A.0000-0002-0644-3799
Chamorro, Eduardo0000-0002-9200-9859
Villegas-Escobar, Nery0000-0002-6370-617X
Cortés-Arriagada, Diego0000-0002-6709-1723
Additional Information:© 2018 American Chemical Society. Received: February 23, 2018; Published: February 27, 2018; Publication Date (Web): February 27, 2018. The authors acknowledge the FONDECYT Grants No. 1140341, No. 1140343, and No. 1170837. N.V.-E. acknowledges the Ph.D. fellowship from CONICYT. We are indebted to Prof. Dr. Rainer Herges for kindly providing us a copy of the ACID software package. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
Fondo Nacional de Desarrollo Científico y Tecnológico (FONDECYT)1140341
Fondo Nacional de Desarrollo Científico y Tecnológico (FONDECYT)1140343
Fondo Nacional de Desarrollo Científico y Tecnológico (FONDECYT)1170837
Comisión Nacional de Investigación Científica y Tecnológica (CONICYT)UNSPECIFIED
Record Number:CaltechAUTHORS:20180319-125008328
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20180319-125008328
Official Citation:Reaction Electronic Flux Perspective on the Mechanism of the Zimmerman Di-π-methane Rearrangement. Ricardo A. Matute, Patricia Pérez, Eduardo Chamorro, Nery Villegas-Escobar, Diego Cortés-Arriagada, Barbara Herrera, Soledad Gutiérrez-Oliva, and Alejandro Toro-Labbé. The Journal of Organic Chemistry 2018 83 (11), 5969-5974. DOI: 10.1021/acs.joc.8b00499
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:85356
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:26 Mar 2018 22:07
Last Modified:04 Jun 2018 23:22

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