The Outcome of the Oxidations of Unusual Enediamide Motifs Is Governed by the Stabilities of the Intermediate Iminium Ions

We compare the results from the oxidation of two unusual “enediamide” motifs (3,4-dihydropyrazin-2(1H)-ones), where a double bond is flanked by two amides. In one case the oxidation led to a ring-opened product arising from the cleavage of the double bond, and in the other a rare cis-dioxygenated co...

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Detalles Bibliográficos
Autores principales: Ahamed, Muneer, Chan, Bun, Jensen, Paul, Todd, Matthew H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Public Library of Science 2012
Materias:
Research Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3477162/
https://www.ncbi.nlm.nih.gov/pubmed/23094038
http://dx.doi.org/10.1371/journal.pone.0047224
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author Ahamed, Muneer
Chan, Bun
Jensen, Paul
Todd, Matthew H.
author_facet Ahamed, Muneer
Chan, Bun
Jensen, Paul
Todd, Matthew H.
author_sort Ahamed, Muneer
collection PubMed
description We compare the results from the oxidation of two unusual “enediamide” motifs (3,4-dihydropyrazin-2(1H)-ones), where a double bond is flanked by two amides. In one case the oxidation led to a ring-opened product arising from the cleavage of the double bond, and in the other a rare cis-dioxygenated compound was obtained. Both products have been characterized by X-ray crystallography. The outcomes of the key reactions are rationalized based on calculated free energies of intermediates.
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spelling pubmed-34771622012-10-23 The Outcome of the Oxidations of Unusual Enediamide Motifs Is Governed by the Stabilities of the Intermediate Iminium Ions Ahamed, Muneer Chan, Bun Jensen, Paul Todd, Matthew H. PLoS One Research Article We compare the results from the oxidation of two unusual “enediamide” motifs (3,4-dihydropyrazin-2(1H)-ones), where a double bond is flanked by two amides. In one case the oxidation led to a ring-opened product arising from the cleavage of the double bond, and in the other a rare cis-dioxygenated compound was obtained. Both products have been characterized by X-ray crystallography. The outcomes of the key reactions are rationalized based on calculated free energies of intermediates. Public Library of Science 2012-10-19 /pmc/articles/PMC3477162/ /pubmed/23094038 http://dx.doi.org/10.1371/journal.pone.0047224 Text en © 2012 Ahamed et al http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are properly credited.
spellingShingle Research Article
Ahamed, Muneer
Chan, Bun
Jensen, Paul
Todd, Matthew H.
The Outcome of the Oxidations of Unusual Enediamide Motifs Is Governed by the Stabilities of the Intermediate Iminium Ions
title The Outcome of the Oxidations of Unusual Enediamide Motifs Is Governed by the Stabilities of the Intermediate Iminium Ions
title_full The Outcome of the Oxidations of Unusual Enediamide Motifs Is Governed by the Stabilities of the Intermediate Iminium Ions
title_fullStr The Outcome of the Oxidations of Unusual Enediamide Motifs Is Governed by the Stabilities of the Intermediate Iminium Ions
title_full_unstemmed The Outcome of the Oxidations of Unusual Enediamide Motifs Is Governed by the Stabilities of the Intermediate Iminium Ions
title_short The Outcome of the Oxidations of Unusual Enediamide Motifs Is Governed by the Stabilities of the Intermediate Iminium Ions
title_sort outcome of the oxidations of unusual enediamide motifs is governed by the stabilities of the intermediate iminium ions
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3477162/
https://www.ncbi.nlm.nih.gov/pubmed/23094038
http://dx.doi.org/10.1371/journal.pone.0047224
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