Intramolecular Phosphine-Promoted Knoevenagel Based Redox-Reaction

A Knoevenagel based redox-reaction promoted by intramolecular phosphine sources is presented for the first time. The influence of different diketones, aldehydes, bases and acids was investigated. The effects of different substituents were evaluated based on their electronical influence on the diketo...

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Autores principales: Feuge, Niklas, Namyslo, Jan C., Kaufmann, Dieter E., Wilhelm, René
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9370043/
https://www.ncbi.nlm.nih.gov/pubmed/35956825
http://dx.doi.org/10.3390/molecules27154875
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author Feuge, Niklas
Namyslo, Jan C.
Kaufmann, Dieter E.
Wilhelm, René
author_facet Feuge, Niklas
Namyslo, Jan C.
Kaufmann, Dieter E.
Wilhelm, René
author_sort Feuge, Niklas
collection PubMed
description A Knoevenagel based redox-reaction promoted by intramolecular phosphine sources is presented for the first time. The influence of different diketones, aldehydes, bases and acids was investigated. The effects of different substituents were evaluated based on their electronical influence on the diketone structure. With the obtained results a mechanism is proposed, giving information about transition states formed during the reaction, which can lead to different products. This type of an internal redox transformation with a phosphine oxide moiety remaining in the molecule after the redox reaction represents a new type of reaction.
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spelling pubmed-93700432022-08-12 Intramolecular Phosphine-Promoted Knoevenagel Based Redox-Reaction Feuge, Niklas Namyslo, Jan C. Kaufmann, Dieter E. Wilhelm, René Molecules Article A Knoevenagel based redox-reaction promoted by intramolecular phosphine sources is presented for the first time. The influence of different diketones, aldehydes, bases and acids was investigated. The effects of different substituents were evaluated based on their electronical influence on the diketone structure. With the obtained results a mechanism is proposed, giving information about transition states formed during the reaction, which can lead to different products. This type of an internal redox transformation with a phosphine oxide moiety remaining in the molecule after the redox reaction represents a new type of reaction. MDPI 2022-07-29 /pmc/articles/PMC9370043/ /pubmed/35956825 http://dx.doi.org/10.3390/molecules27154875 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Feuge, Niklas
Namyslo, Jan C.
Kaufmann, Dieter E.
Wilhelm, René
Intramolecular Phosphine-Promoted Knoevenagel Based Redox-Reaction
title Intramolecular Phosphine-Promoted Knoevenagel Based Redox-Reaction
title_full Intramolecular Phosphine-Promoted Knoevenagel Based Redox-Reaction
title_fullStr Intramolecular Phosphine-Promoted Knoevenagel Based Redox-Reaction
title_full_unstemmed Intramolecular Phosphine-Promoted Knoevenagel Based Redox-Reaction
title_short Intramolecular Phosphine-Promoted Knoevenagel Based Redox-Reaction
title_sort intramolecular phosphine-promoted knoevenagel based redox-reaction
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9370043/
https://www.ncbi.nlm.nih.gov/pubmed/35956825
http://dx.doi.org/10.3390/molecules27154875
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AT namyslojanc intramolecularphosphinepromotedknoevenagelbasedredoxreaction
AT kaufmanndietere intramolecularphosphinepromotedknoevenagelbasedredoxreaction
AT wilhelmrene intramolecularphosphinepromotedknoevenagelbasedredoxreaction

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