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Identifier 000451444
Title Υδροσιλυλίωση ή αφυδρογονωτική υδροσιλυλίωση αρυλο-υποκατεστημένων κυκλοπροπυλο καρβονυλικών ενώσεων με διάνοιξη δακτυλίου καταλυόμενη από νανοσωματίδια Au
Alternative Title Ring-opening hydrosilylation or dehydrogenative hydrosilylation of aryl-substituted cyclopropyl carbonyl compounds catalyzed by Au nanoparticles
Author Ζαχίλας, Ιωάννης Α.
Thesis advisor Στρατάκης, Εμμανουήλ
Reviewer Βασιλικογιαννάκης, Γεώργιος
Σμόνου, Ιουλία
Abstract Ιn this dissertation we present the reaction between hydrosilanes and aryl-substituted cyclopropyl aldehydes or ketones catalyzed by Au nanoparticles supported on TiO2 that provides two distinct ring-opening reaction motifs depending on the substituents. 2- Aryl-substituted cyclopropyl carbonyl compounds form linear enol ethers via formal silyl hydride addition on the carbon atom bearing the aryl group. Under the reaction conditions the hydrosilylation adducts undergo silyl-deprotection leading to linear aldehydes or ketones. For 2,2-arylalkyl- or 2,2-diaryl-substituted cyclopropyl carbonyl compounds, ring-opening dehydrogenative hydrosilylation is observed forming chromatographically stable silyloxy 1,3-dienes. In the presence of TEMPO the reaction is inhibited, thus a radical pathway is proposed. The proposed intermediate acyclopropyl silyloxy radicals undergo radical-clock ring opening to form benzyl radicals, which may either be captured by the hydrosilane H atom (for 2-aryl-substituted substrates) to form linear silyl enol ethers, or eliminate H2 and form silyloxy 1,3-dienes (in the case of the bulkier 2,2-disubstituted ones).
Language Greek, English
Issue date 2022-11-24
Collection   School/Department--School of Sciences and Engineering--Department of Chemistry--Post-graduate theses
  Type of Work--Post-graduate theses
Permanent Link https://elocus.lib.uoc.gr//dlib/9/d/2/metadata-dlib-1664969407-1038-8857.tkl Bookmark and Share
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