Mechanochemical Knoevenagel condensations of benzaldehyde derivates investigated in situ

  • Mechanochemistry is widely applicable for the synthesis of inorganic, metal-organic, and organic compounds. It is known for short reaction times, nearly quantitative conversions, and decreasing amount of solvents, which opens the field to more environmentally friendly syntheses routes. Among organic syntheses, the Knoevenagel condensation is an important C-C bond forming reaction leading to α,β-unsaturated compounds. To gain more information on the underlying processes, we investigated the syntheses by a combination of different in situ investigation techniques, including synchrotron X-ray diffraction, Raman spectroscopy and thermography. This combination provides information on the structural changes and temperature influences during milling. Benzaldehyde derivates (nitro- and fluoro-derivates) reacted with malononitrile to the respective benzylidenemalononitriles. The in situ investigations show direct and quantitative conversions. In the case of the fluorinated benzaldehydeMechanochemistry is widely applicable for the synthesis of inorganic, metal-organic, and organic compounds. It is known for short reaction times, nearly quantitative conversions, and decreasing amount of solvents, which opens the field to more environmentally friendly syntheses routes. Among organic syntheses, the Knoevenagel condensation is an important C-C bond forming reaction leading to α,β-unsaturated compounds. To gain more information on the underlying processes, we investigated the syntheses by a combination of different in situ investigation techniques, including synchrotron X-ray diffraction, Raman spectroscopy and thermography. This combination provides information on the structural changes and temperature influences during milling. Benzaldehyde derivates (nitro- and fluoro-derivates) reacted with malononitrile to the respective benzylidenemalononitriles. The in situ investigations show direct and quantitative conversions. In the case of the fluorinated benzaldehyde derivates we showed the possibility of using liquid substrates in mechanochemical organic synthesis. Surprisingly, after crystallization from a viscous state, the material was suitable for single-crystal X-ray analysis.zeige mehrzeige weniger

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Metadaten
Autor*innen:Sebastian Haferkamp
Koautor*innen:Irina Akhmetova, Hannes Kulla, K. Rademann, Franziska Emmerling
Dokumenttyp:Posterpräsentation
Veröffentlichungsform:Präsentation
Sprache:Englisch
Jahr der Erstveröffentlichung:2018
Organisationseinheit der BAM:6 Materialchemie
6 Materialchemie / 6.3 Strukturanalytik
DDC-Klassifikation:Naturwissenschaften und Mathematik / Chemie / Analytische Chemie
Technik, Medizin, angewandte Wissenschaften / Ingenieurwissenschaften / Ingenieurwissenschaften und zugeordnete Tätigkeiten
Freie Schlagwörter:C-C coupling; In situ; Knoevenagel; Mechanochemistry
Themenfelder/Aktivitätsfelder der BAM:Chemie und Prozesstechnik
Material
Veranstaltung:Powder Diffraction School 2018
Veranstaltungsort:Villigen, Switzerland
Beginndatum der Veranstaltung:24.09.2018
Enddatum der Veranstaltung:28.09.2018
Verfügbarkeit des Dokuments:Datei im Netzwerk der BAM verfügbar ("Closed Access")
Datum der Freischaltung:18.10.2018
Referierte Publikation:Nein
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