Organokatalytická oxidace sulfidů v micelárních systémech obsahujících amfifilní flaviniové soli s využitím peroxidu vodíku jako terminálního oxidačního činidla

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F07%3A00018488" target="_blank" >RIV/60461373:22310/07:00018488 - isvavai.cz</a>

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Organocatalytic sulfoxidation in micellar systems containing amphiphilic flavinium salts using hydrogen peroxide as a terminal oxidant

Popis výsledku v původním jazyce

Amphiphilic flavinium salt [10-dodecyl-5-ethyl-3,7,8-trimethylisoalloxazinium perchlorate (1b)], solubilized in micelles of sodium dodecyl sulfate (SDS), hexadecyltrimethylammonium chloride (CTAC), hexadecyltrimethylammonium nitrate (CTANO3) or Brij 35,catalyzes the chemoselective oxidation of thioanisole (2) to its corresponding sulfoxide 4. The sulfoxidation rates observed in micelles in the presence of 1b exceeded, in most instances, those of the reaction catalyzed by its hydrophilic homologue [5-ethyl-3,7,8,10-tetramethylisoalloxazinium perchlorate (1a)] in a homogeneous solution. Reaction rates were strongly dependent on the type of micellar matrix and on the pH value. The highest acceleration rates were found in SDS micelles at pH 4.4 (TOF = 3 x103 h-1). In our experiments, micelles favoured the catalytic process rather than the non-catalyzed reaction, this effect being especially pronounced in cationic micelles, for which the non-catalyzed reaction was markedly suppressed. The

Název v anglickém jazyce

Organocatalytic sulfoxidation in micellar systems containing amphiphilic flavinium salts using hydrogen peroxide as a terminal oxidant

Popis výsledku anglicky

Amphiphilic flavinium salt [10-dodecyl-5-ethyl-3,7,8-trimethylisoalloxazinium perchlorate (1b)], solubilized in micelles of sodium dodecyl sulfate (SDS), hexadecyltrimethylammonium chloride (CTAC), hexadecyltrimethylammonium nitrate (CTANO3) or Brij 35,catalyzes the chemoselective oxidation of thioanisole (2) to its corresponding sulfoxide 4. The sulfoxidation rates observed in micelles in the presence of 1b exceeded, in most instances, those of the reaction catalyzed by its hydrophilic homologue [5-ethyl-3,7,8,10-tetramethylisoalloxazinium perchlorate (1a)] in a homogeneous solution. Reaction rates were strongly dependent on the type of micellar matrix and on the pH value. The highest acceleration rates were found in SDS micelles at pH 4.4 (TOF = 3 x103 h-1). In our experiments, micelles favoured the catalytic process rather than the non-catalyzed reaction, this effect being especially pronounced in cationic micelles, for which the non-catalyzed reaction was markedly suppressed. The

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/1K04105" target="_blank" >1K04105: Nové katalyzátory oxidačních reakcí založené na amfifilních flavinech</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2007

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Molecular Catalysis

ISSN

1381-1169

e-ISSN

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Svazek periodika

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Číslo periodika v rámci svazku

277

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

8

Strana od-do

53-60

Kód UT WoS článku

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EID výsledku v databázi Scopus

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