"[3CB725BE4309]" . . "22310" . "Cibulka, Radek" . . . "RIV/60461373:22310/07:00018488!RIV08-MSM-22310___" . "3"^^ . "53-60" . "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 x 103 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 ratio vcat / v0"@en . . . "2"^^ . . "Amfifiln\u00ED flaviniov\u00E1 s\u016Fl [10-dodecyl-5-ethyl-3,7,8-trimethylisoalloxazinium-perchlor\u00E1t (1b)], solubilizovan\u00E1 v micel\u00E1ch dodecylsulfon\u00E1tu sodn\u00E9ho (SDS), hexadecyltrimethylammonium-chloridu (CTAC), hexadecyltrimethylammonium-nitr\u00E1tu (CTANO3) a Brij 35, katalyzuj\u00ED chemoselektivn\u00ED oxidaci thioanisolu na odpov\u00EDdaj\u00EDc\u00ED sulfoxid. Rychlost oxidace v micel\u00E1rn\u00EDch syst\u00E9mech v p\u0159\u00EDtomnosti 1b ve v\u011Bt\u0161in\u011B p\u0159\u00EDpad\u016F p\u0159ed\u010D\u00ED rychlost reakce katalyzovanou hydrofiln\u00EDm deriv\u00E1tem [5-ethyl-3,7,8,10-tetramethylisoalloxazinium-perchlor\u00E1tem (1a)] v homogenn\u00EDm prost\u0159ed\u00ED. Reak\u010Dn\u00ED rychlost z\u00E1vis\u00ED siln\u011B na pH a na pou\u017Eit\u00E9 micel\u00E1rn\u00ED matrici. Nejrychleji prob\u00EDhala reakce v SDS p\u0159i pH 4.4 (TOF = 3 x 103 h-1). Nejv\u00FDrazn\u011Bj\u0161\u00ED urychlen\u00ED katalyzovan\u00E1 vs nekatalyzovan\u00E1 reakce vcat / v0 = 40 bylo pozorov\u00E1no v CTANO3. V homogenn\u00EDm prost\u0159ed\u00ED toto urychlen\u00ED nep\u0159es\u00E1hlo hodnotu 7."@cs . "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 x 103 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 ratio vcat / v0" . "Organocatalytic sulfoxidation in micellar systems containing amphiphilic flavinium salts using hydrogen peroxide as a terminal oxidant"@en . "Organocatalytic sulfoxidation in micellar systems containing amphiphilic flavinium salts using hydrogen peroxide as a terminal oxidant" . "Baxov\u00E1, Lenka" . . "NL - Nizozemsko" . . "Organocatalytic sulfoxidation in micellar systems containing amphiphilic flavinium salts using hydrogen peroxide as a terminal oxidant" . . "277" . . "Journal of Molecular Catalysis" . . "Organokatalytick\u00E1 oxidace sulfid\u016F v micel\u00E1rn\u00EDch syst\u00E9mech obsahuj\u00EDc\u00EDch amfifiln\u00ED flaviniov\u00E9 soli s vyu\u017Eit\u00EDm peroxidu vod\u00EDku jako termin\u00E1ln\u00EDho oxida\u010Dn\u00EDho \u010Dinidla"@cs . . . "Organokatalytick\u00E1 oxidace sulfid\u016F v micel\u00E1rn\u00EDch syst\u00E9mech obsahuj\u00EDc\u00EDch amfifiln\u00ED flaviniov\u00E9 soli s vyu\u017Eit\u00EDm peroxidu vod\u00EDku jako termin\u00E1ln\u00EDho oxida\u010Dn\u00EDho \u010Dinidla"@cs . "Sulfoxidation; Micelles; Organocatalysis; Green chemistry; Flavinium salts"@en . "P(1K04105)" . . . . "8"^^ . "440023" . . "1381-1169" . "Organocatalytic sulfoxidation in micellar systems containing amphiphilic flavinium salts using hydrogen peroxide as a terminal oxidant"@en . . "RIV/60461373:22310/07:00018488" . "Hampl, Franti\u0161ek" .