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Faculté des Sciences
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Development of continuous flow processes for the oxidative preparation of nitrosoarenes

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Macors, Elyse ULiège
Promotor(s) : Monbaliu, Jean-Christophe ULiège
Date of defense : 18-Jan-2023 • Permalink : http://hdl.handle.net/2268.2/17025
Details
Title : Development of continuous flow processes for the oxidative preparation of nitrosoarenes
Translated title : [fr] Développement de processus en flux continu pour la préparation de nitrosoarènes par oxydation.
Author : Macors, Elyse ULiège
Date of defense  : 18-Jan-2023
Advisor(s) : Monbaliu, Jean-Christophe ULiège
Committee's member(s) : Lecomte, Philippe ULiège
Silva Brenes, Diana Vanessa ULiège
Tsai, Yi-Hsuan ULiège
Monbaliu, Jean-Christophe ULiège
Language : English
Number of pages : 67
Keywords : [en] Nitrosoarenes synthesis
[en] continuous flow
[en] Aniline catalyzed oxidation
[en] computational chemistry
Discipline(s) : Physical, chemical, mathematical & earth Sciences > Chemistry
Research unit : Center for integrated Technology and Organic Synthesis
Target public : Researchers
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Student
Institution(s) : Université de Liège, Liège, Belgique
Degree: Master en sciences chimiques, à finalité approfondie
Faculty: Master thesis of the Faculté des Sciences

Abstract

[en] Nitrosoarenes are widely used in organic synthesis and medicinal chemistry. Despite their low commercial availability, those compounds are bench stable and could be isolated after synthesis for further reactions. However, nitrosoarenes synthesis is challenging due to its lack of selectivity leading to cumbersome, time- and resource-intensive purification method. A lab-scale flow setup has been developed for the tungstate-catalyzed aniline oxidation by hydrogen peroxide to have better selectivities. This setup led to similar selectivities than in batch but remains interesting for its easy scalability. Computations were also performed to support the experimental part. With it, oxidation potentials were determined leading to a better understanding of the aniline reactivity. Based on those results, a temperature-oxidation potential scale was constructed and verified. This one is not linear and does not consider the steric effects. Thus, the o-substituted anilines would have another scale than the other substituted anilines. Moreover, an improvement of the scale is possible by preparing more nitrosoarenes under flow conditions.


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  • Macors, Elyse ULiège Université de Liège > Master en sc. chimiques, à fin.

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