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Verification of flavinium salts reactivity with N- and O-nucleophiles for eventual transformation of boronic acids to corresponding amines
Honskusová, Linda ; Kotoučová, Hana (advisor) ; Holakovský, Roman (referee)
Presented diploma thesis follows the long-term study running at the Department of Organic Chemistry at the University of Chemistry and Technology Prague in the field of using flavinium salts as catalysts of oxidation reactions. The aim was to verify the reactivity of flavinium salt 13 with different types of O- and N-nucleophiles by monitoring of the corresponding C4a-adducts formation. In the thesis a simple alloxazinium salt 13 and one of the nucleophiles (hydroxylamine 25) were prepared. According to the results obtained from the UV-VIS measurements nucleophile 25 is the only one of the newly tested wchich formed desired C4a-adduct 13d with alloxazinium salt 13. KEYWORDS flavinium salt, nucleophile, C4a-adduct, organocatalysis, IBSE
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Verification of flavinium salts reactivity with N- and O-nucleophiles for eventual transformation of boronic acids to corresponding amines
Honskusová, Linda ; Kotoučová, Hana (advisor) ; Holakovský, Roman (referee)
Presented diploma thesis follows the long-term study running at the Department of Organic Chemistry at the University of Chemistry and Technology Prague in the field of using flavinium salts as catalysts of oxidation reactions. The aim was to verify the reactivity of flavinium salt 13 with different types of O- and N-nucleophiles by monitoring of the corresponding C4a-adducts formation. In the thesis a simple alloxazinium salt 13 and one of the nucleophiles (hydroxylamine 25) were prepared. According to the results obtained from the UV-VIS measurements nucleophile 25 is the only one of the newly tested wchich formed desired C4a-adduct 13d with alloxazinium salt 13. KEYWORDS flavinium salt, nucleophile, C4a-adduct, organocatalysis, IBSE
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Flavinium Salts Usage as Catalysts of Oxidation Reactions
Strnadová, Iveta ; Kotoučová, Hana (advisor) ; Holakovský, Roman (referee)
Usage of Flavinium Salts as Catalysts of Oxidation Reactions Summary This diploma thesis deals with use of flavinium salts as a catalysts of oxidation reactions. 3,7,8,10-tetramethylisoalloxazin 25, 5-ethyl-3,7,8,10-tetramethylisoalloxazinium perchlorate 16 and 5-ethyl-1,3-dimethylalloxazinium perchlorate 26 had been prepared. Salts 16, 26 and other previously prepared phlavinium salt 28 were tested as potential catalysts for the oxidation of phenylboronic acids to the corresponding phenols, and especially for the use of oxygen as the oxidizing agent. The best solvent systems were found through testing and followed possible influence of the substituent on the phenyl ring of boronic acid was investigated. This initial screening can be used as a basis for further and more detailed testing of catalytic efficiency of flavinium salts and to study the oxidation mechanism.
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